Laboratorium voor Medicinale Chemie

A. Samenstelling van de onderzoeksgroep

Zelfstandig Academisch Personeel

Herdewijn P., gewoon hoogleraar

Claes P., hoogleraar (em. 2000)

Busson R., hoogleraar

Rozenski J., hoofddocent

Van Aerschot A., onderzoeksleider FWO, deeltijds hoofddocent

Janssen G., hoofddocent (em. 1998)

Assisterend Academisch Personeel (doctorandi)

Ceulemans G., assistent, 1992-1997

Samson I., assistent, 1992-1997

Verbeure B., assistent, 1995 _ heden

Chaltin P., assistent, 1997 - heden

Doctorandi

Lescrinier T., 1993-1997.

Lescrinier E., 1995-1999.

Marangoni M., 1994-1997.

Zhang Z., 1997-2000

Raskin D., 1998-2000

Vastmans K., 1998-heden

Gu P., 1999-heden

Post-doctoraal Onderzoekers

Dr. C. Hendrix, 1996-2000

Dr. S. Mikhailov, Engelhardt Institute of Molecular Biology, Russian Academy of

Sciences, 1999-2000.

Dr. I. Luyten, 1997-2000.

Dr. N. Hossain, Department of Bioorganic Chemistry, Biomedical Center, Uppsala,

Sweden, 1995-1997.

Dr. Y. Maurinsh, Latvian Institute of Organic Synthesis, Latvia, 1995-1996, 1997.

Dr. H. De Winter, 1995-1996.

Dr. E. Lescrinier, Navorser NFWO 1999-.heden

Prof. Dr. J. Schraml, Institute of Chemical Process Fundamentals, Academy of

Sciences of the Czech Republic and University of Chemical Technology, Prague,

1995-1996.

Dr. B. Allart, Université de Reims Champagne-Ardenne, Reims, France, 1995-1997.

Dr. T. Ostrowski, A. Mickiewicz University, Poznan, Poland, 1996-1997.

Dr. J. Wang, University of Bern, Institute of Organic Chemistry, Switzerland, 1997-

heden

Prof. Dr. H. Van Halbeek, University of Georgia, Athens, Georgia, U.S.A., 1996-

1997.

Dr. Berthold Wroblowski, Institute for Biochemistry of the RWTH, Aachen,

Germany, 1996-1998.

Dr. Mahmoud Aloui, University of St. Andrews, St. Andrews, Scotland, 1998-

1999.

Dr. Stephen Turner, University of Southampton, Southampton, U.K., 1997.

Dr. Klaus Rothenbacher, Universität Ulm, European large-scale facility lab,

Napels,.1997-1998

Dr. Valérie Boudou, Université de Languedoc, Montpellier, France, 1997-1998.

Dr. Mattheus Froeyen, 1998- heden

Dr. Carl Jeffrey Lacey, Lehigh University, Dept. Chemistry, 1999-heden,

Dr. Irene Lagoja, Leopold-Franzens University, Innsbruck, Austria, 1999-heden

Dr. Michael Meldgaard, University of Copenhagen, Dept. Chemistry, Denmark,

1999

Dr. Jordi Morral, Universidad de Barcelona, Facultad de Farmacia, Barcelona, Spain,

1999-2000

Prof. Roy Little, Ph.D., University of Florida, Depto de Quimica, Universitad de los

Andes, Venezuela, 2000 - heden

Dr. E. Efimtseva, Engelhardt Institute of Molecular Biology, Moskow, Russia, 2000

Administratief en Technisch Personeel

Vandekinderen M., secretaresse, 1992 - 1998

Biernaux C., secretaresse K.U.Leuven, 1998 - heden

Baudemprez L., technicus, K.U.Leuven, 1998 - heden

Kerremans L., hoofdlaborant, K.U.Leuven,

Schepers G., laborant, 1990 - heden

Vandeneynde W., laborant, 1998 - heden

B. Onderzoeksactiviteiten

Onderzoek naar nieuwe biologisch actieve nucleoside analogen heeft geleid tot het

op punt stellen van een reeks synthesemethoden voor nucleosiden waarbij de

klassieke furanose ring werd vervangen door een zesring. Voorbeelden van nieuwe

nucleoside analogen die werden gesynthetiseerd zijn vertakte nucleosiden,

homonucleosiden, hexitol nucleosiden, cyclohexaan nucleosiden, cyclohexeen

nucleosiden, hydroxyprolinol nucleosiden, disaccharide nucleosiden.

Verschillende van deze nucleoside analogen werden omgezet in hun fosforamidieten

en geïncorporeerd in oligonucleotiden waarvan de eigenschappen werden

bestudeerd. Het doel hiervan is enerzijds de ontwikkeling van antisense

therapeutica en anderzijds het ontrafelen van de structurele voorwaarden van

oligonucleotiden voor hybridisatie met RNA en voor enzymactivatie.

Er werd vastgesteld dat hexitol nucleïnezuren een goede affiniteit bezitten voor

RNA, doch hun biologische activiteit was minder goed dan verwacht (omwille van

de afwezigheid van activatie van RNA hydrolyserende enzymen). Structurele

studies met hexitol nucleïnezuren, gecomplexeerd met RNA, werden uitgevoerd

met behulp van NMR, waardoor een verklaring kon worden bekomen voor de

afwezigheid van de hoger vernoemde enzymatische activiteit. Hexitol

nucleïnezuren (zoals altritol nucleïnezuren) blijken een goed templaat te zijn voor

niet-enzymatische gekatalyseerde polymerisatie reacties. De enzymatisch

gekatalyseerde polymerisatie verloopt minder efficiënt. De cyclohexaan en

mannitol oligonucleotides zijn interessante modellen voor conformationele studies

van RNA. Bijzondere aandacht werd besteed aan de enantioselectieve synthese

van cyclohexeen nucleosiden. Oligonucleotiden opgebouwd uit cyclohexeen

fragmenten induceren Rnase H, hetgeen een zeldzame waarneming is in het domein

van synthetische RNA/DNA.

Een aanvang werd genomen met de studie van de incorporatie van gemodificeerde

nucleosiden in RNA (tRNA) en hun invloed op de structuur van RNA-hairpins.

Modelling studies werden uitgevoerd om de bindingen van nucleoside analogen aan

thymidine kinasen beter te begrijpen en te kwantificeren en om de structuur en

dynamica te onderzoeken van artificiële oligonucleotiden. NMR studies werden

uitgevoerd om het evenwicht te bestuderen tussen verschillende conformaties van

DNA-oligomeren en vooral om de structuur van hairpins te onderzoeken.

Daarnaast werd ook aandacht besteed aan het ontwikkelen van

peptidenbibliotheken, voornamelijk voor de sequentiespecifieke herkenning van

DNA. Hiervoor werden synthesemethoden ontwikkeld voor de nieuwe niet-

natuurlijke aminozuren en hun incorporatie in oligopeptides werd nagegaan. Een

screeningsmethode in vaste fase voor DNA-bindende liganden werd ontwikkeld,

gebruik makend van gemerkt DNA.

Verschillende biologisch actieve moleculen werden ontwikkeld en dit in het domein

van herpesvirussen, adenosine receptoren, P2Y1 receptoren en moleculen die in

staat zijn om neurongroei te activeren.

C.Dienstverlening

Er werden massaspectra en NMR spectra opgenomen en geïnterpreteerd voor

laboratoria binnen en buiten de universiteit.

Structuur van een HNA-RNA duplex in oplossing (PDB-nummer: 1EJZ)Zicht in de mineure groeve van de hoge resolutie structuur van een HNA achtmeer (groen lint doorC1') gebonden aan een complementaire RNA keten (rood lint door O4'), die werd bepaald doormiddel van NMR spectroscopie. Het HNA-RNA complex vormt een anti-parallelle heteroduplex enneemt een helicale conformatie aan die behoort tot de groep van A-type helixen. Door de starrestoelconformatie van de hexitol zesringen, zijn zowel de HNA an RNA keten in de duplex goedgedefinieerd. De P-P afstand over de mineure groeve (paarse linten) en de starre structuur van deHNA-RNA duplex, verklaren de resistentie van het complex voor afbraak door RNase H. Het A-helixkarakter van de duplex en de beperkte flexibiliteit van de HNA keten in vergelijking met natuurlijkenucleïnezuren, zijn mogelijk verantwoordelijk voor de stereoselectiviteit van HNA templaten bij niet-enzymatische replicatie van oligonucleotiden. Dit ondesteunt de theorie dat nucleosiden metzesring-suikers zouden hebben bestaan in een stadium van de moleculaire evolutie.(Lescrinier, E., Esnouf, R., Schraml, J., Busson, R., Heus, H., Hilbers C. and Herdewijn, P. 2000Chem. Biol. 7: 719-731)

D. Lijst van publicaties, voordrachten, mededelingen

I. Artikels in internationale gereviewde tijdschriften

1996

Declercq R, Herdewijn P, Van Meervelt L. 1,5-anhydro-2,3-dideoxy-2-(guanin-9-yl)-D-arabino-hexitol, Acta Cryst. 1996; C52:1213-1215.

Creuven I, Evrard C, Olivier A, Evrard G, Van Aerschot A, Wigerinck P, HerdewijnP, Durant F. Relationship between structural properties and affinity for HSV-1kinase of bromine substituted 5-heteroaromatic 2'-deoxyuridines, Antiviral Res.1996; 30:63-74.

Hendrix C, Anné J, Joris B, Van Aerschot A, Herdewijn P. Selection ofHammerhead Ribozymes for optimum cleavage of interleukin 6 mRNA, Biochem.J. 1996; 314(2):655-661.

Mikhailov SN, Blaton N, Rozenski J, Balzarini J, De Clercq E, Herdewijn P. Use ofcyclohexene epoxides in the preparation of carbocyclic nucleosides, NucleosidesNucleotides 1996; 15:867-878.

Mikhailov S, De Clercq E, Herdewijn P. Ribosylation of pyrimidine 2'-deoxynucleosides, Nucleosides Nucleotides 1996; 15:1323-1334.

Doboszewski B, Herdewijn P. Branched-chain nucleosides: synthesis of 3'-deoxy-3'-C-hydroxy-methyl-α-L-lyxopyranosylthymine and 3'-deoxy-3'-C-hydroxymethyl-α-L-threofuranosylthymine, Tetrahedron 1996; 52:1651-1668.

Verheggen I, Van Aerschot A, Rozenski J, Janssen G, De Clercq E, Herdewijn P.Synthesis of 1,5-anhydrohexitol nucleosides as mimics of AZT, D4T and DDC,Nucleosides Nucleotides 1996; 15:325-335.

Doboszewski B, Herdewijn P. Synthesis of 4-deoxy-4-C-hydroxymethyl-α-L-lyxopyranosyl thymine, Nucleosides Nucleotides 1996; 15:1495-1518.

Hossain N, Blaton N, Peeters O, Rozenski J, Herdewijn P. Synthesis of homo-N-nucleosides, a series of C1Z branched chain nucleosides, Tetrahedron 1996;52:5563-5578.

Efimtseva EV, Ermolinsky BS, Fomitcheva MV, Meshkov S, Padyukova N,Mikhailov SN, Van Aerschot A, Rozenski J, Herdewijn P. Synthesis of disaccharidenucleosides and their incorporation into oligonucleotides, Coll. Czech. Chem.Commun. 1996; 61 SI:206-209.

Mikhailov SN, Efimtseva EV, Ermolinski B, Fomitcheva, M, Gritsenko O, BrevnovM, Gromova E, Schepers G, Van Aerschot A, Herdewijn P. Regioselectiveincorporation of reactive dialdehyde groups into synthetic oligonucleotides, Coll.Czech. Chem. Commun. 1996; 61 SI:210-213.

Lescrinier T, Busson R, Janssen G, Rozenski J, Van Aerschot A, Herdewijn P.Incorporation of 5-hydroxytryptophan in oligopeptides, Tetrahedron 1996;52:6965-6972.

Luyten I, De Winter H, Busson R, Lescrinier T, Creuven I, Durant F, Balzarini J, DeClercq E, Herdewijn P. Synthesis of 5-(isothiazol-5-yl)-2Z-deoxyuridine and itsinteraction with HSV-1 thymidine kinase, Helv. Chim. Acta. 1996; 79:1462-1474.

Hossain N, Hendrix C, Lescrinier E, Van Aerschot A, Busson R, De Clercq E,Herdewijn P. Homo-N-nucleosides : incorporation into oligonucleotides and antiviralactivity, Bioorg. Med. Chem. Lett. 1996; 6:1465-1468.

Pérez-Pérez M.-J, De Clercq E, Herdewijn P. Synthesis and antiviral activity of 2-deoxy-1,5-anhydro-D-mannitol nucleosides containing a pyrimidine base moiety,Bioorg. Med. Chem. Lett. 1996; 6:1457-1460.

Luyten I, Herdewijn P. Synthesis and conformational behavior of purine andpyrimidine β-D-threo-hex-3Z-enopyranosyl nucleosides, Tetrahedron 1996; 52:9249-9262.

Ceulemans G, Herdewijn P. Nucleosides and oligonucleotides derived from trans-4-hydroxy-N-acetyl prolinol, Coll. Czech. Chem. Commun. 1996; 61 SI:234-237.

Marangoni M, Van Aerschot A, Augustyns P, Herdewijn P. Cyclopenthylethylnucleosides as ^constrained] acyclic building blocks for oligonucleotides, Coll.Czech. Chem. Commun. 1996; 61 SI:203-205.

Herdewijn P. Targeting RNA with conformational restricted oligonucleotides, LiebigsAnnalen 1996; 9:1337-1348.

Herdewijn P. Oligonucleotides with ability to inhibit cytomegalovirus, ExpertOpinion Ther. Patents 1996; 6:1-3.

Van Veldhoven P, Croes K, Asselberghs S, Herdewijn P, Mannaerts G, Peroxisomalβ-oxidation of 2-methyl-brached acyl-CoA esters : stereospecific recognition of the2S-methyl compounds by trihydroxy copristanoyl-CoA oxidase and pristanoyl CoAoxidase, FEBS Lett. 1996; 388(1):80-84.

Hossain N, Rozenski J, De Clercq E, Herdewijn P. Synthesis and antiviral activityof acyclic analogues of 1,5-anhydrohexitol nucleosides using Mitsunobu reaction,Tetrahedron 1996; 52:13655-13670.

De Winter H, Herdewijn P. Understanding the binding of 5-substituted 2Z-deoxy-uridine substrate to thymidine kinase of Herpes Simplex Virus type 1, J. Med.Chem. 1996; 39:4727-4737.

Andersen M, Daluge S, Kerremans L, Herdewijn P. The synthesis of modified D-and L-anhydrohexitol nucleosides, Tetrahedron Lett. 1996; 37:8147-8150.

Creuven I, Norberg B, Olivier A, Evrard C, Evrard G, Wigerinck P, Herdewijn P,Durant F, 5-(thien-2-yl)uracil analogues : 5-(5-methylthien-2-yl)-2'-deoxyuridine, 5-(5-thien-2-yl)-2'-deoxyuridine and 5-(5-bromothien-2-yl)-2'-deoxyuridine, J.Chemical Crystallography 1996; 26:777-789.

Lescrinier E, Pannecouque C, Van Aerschot A, Kerremans L, Herdewijn P.

Synthesis of N6-alkylated adenosine derivatives, Nucleosides Nucleotides 1996;

15:1863-1869.

1997

Thioithi G, Van Schepdael A, Herdewijn P, Roets E, Hoogmartens J, Liquidchromatographic separation of hexopyranosylated cytosine nucleosides from theirdegradation product, J. Pharm. Biomed. Analysis 1997; 16:533-540.

Mikhailov S, Efimtseva E, Gurskaya G, Fomitcheva, M, Meshkov S, Zavodnik V, DeBruyn A, Janssen G, Rozenski J, Herdewijn P. An efficient synthesis andphysicochemical properties of 2'-O-D-ribofuranosyl nucleosides, minor tRNAcomponents, J. Carbohydr. Chem. 1997; 16:75-92.

Hendrix C, Verheggen I, Rosemeyer H, Seela F, Van Aerschot A, Herdewijn P.1',5'-Anhydrohexitol oligonucleotides: synthesis, base pairing and recognition byregular oligodeoxyribonucleotides and oligoribo-nucleotides, Chemistry Eur. J.1997; 3:110-120.

Lescrinier T, Busson R, De Winter H, Hendrix C, Janssen G, C. Pannecouque,Rozenski J, Van Aerschot A, Herdewijn P. α-Amino acids derived from ornithine asbuilding blocks for peptide synthesis, J. Peptide Res. 1997; 49:183-189.

Saeyens W, De Keukeleire D, Herdewijn P, De Bruyn A, Access to stericallyconfirmed nucleoside analogues via intramolecular photocyclo additions of arene-alkene trichromophores, Biomedical Chromatography 1997; 11:79-80.

Brevnov MG, Gritsenko OM, Mikhailov SN, Efimtseva EV, Ermolinsky BS, VanAerschot A, Herdewijn P, Rèpyk AV, Gromova ES. DNA duplexes with reactivedialdehyde groups as novel reagents for cross-linking to restriction modificationenzymes, Nucleic Acids Research. 1997; 25:3302-3309.

Creuven I, Lebon F, Busson R, Herdewijn P, Durant F, Structural study of two 5-heteroaromatic-2Z-deoxyuridines and their 5-bromine-heteroaromatic analogues:theoretical conformational analysis and NMR experiments, Nucleosides Nucleotides1997; 16:339-346.

Van Calenbergh S, De Bruyn A, Schraml J, Blaton N, Peeters O, De Keukeleire D,Busson R, Herdewijn P. Access to a new type of homo-C-nucleotides with a ^split]8-deazapurine in a 1,3-dipolar cycloaddition reaction, Nucleosides Nucleotides1997; 16:291-300.

De Bruyn A, Maras M, Schraml J, Herdewijn P, Contreras R, NMR evidence for anovel asparagine-linked oligosaccharide on cellobiohydrolase I from Trichodermareesei RUTC 30, FEBS Lett. 1997; 405:111-113.

Wuyts A, Van Osselaer N, Haelens A, Samson I, Herdewijn P, Ben-Baruch A,Oppenheim J, Proost P, Van Damme J, Characterization of synthetic humangranulocyte chemotactic protein 2: usage of chemokine receptors CXCR1 andCXCR2 and in vivo inflammatory properties, Biochemistry 1997; 36:2716-2723.

Schraml J, De Bruyn A, Contreras R, Herdewijn P. A versatile NMR technique forthe identification of phosphorylation sites in oligosaccharides, J. Carbohydr. Chem.1997; 16:165-170.

Luyten I, Van Aerschot A, Rozenski J, Busson R, Herdewijn P. Protection of 2,6-diaminopurine 2Z-deoxyribose, Nucleosides Nucleotides 1997; 16:1649-1652.

De Bouvere B, Kerremans L, Hendrix C, De Winter H, Schepers G, Van AerschotA, Herdewijn P. Hexitol nucleic acids (HNA): synthesis and properties, NucleosidesNucleotides 1997; 16:973-976.

Saeyens W, Busson R, Van der Eycken J, Herdewijn P, De Keukeleire D, Fullyselective intramolecular ortho photocycloaddition of 4-(4-methoxyphenoxy)-3-(N3-benzoylthymin-1-yl)but-1-ene: an unprecedent benzene-thymine photocycloaddition,J. Chem. Soc. Chem. Commun. 1997:817-818.

Hossain N, Rozenski J, De Clercq E, Herdewijn P. Synthesis and antiviral activityof the α -analogues of 1,5-anhydrohexitol nucleosides (1,5-anhydro-2,3-dideoxy-D-ribohexitol nucleosides), J. Org. Chem. 1997; 62:2442-2447.

Maras M, De Bruyn A, Schraml J, Herdewijn P, Claeyssens M, Fiers W, ContrerasR, Structural characterisation of N-linked oligosaccharides from cellobiohydrolaseI secreted by the filamentous fungus Trichoderma reesei RUTC 30, Eur. J.Biochem. 1997; 245:617-625.

Samson I, Rozenski J, Samyn B, Van Aerschot A, Van Beeumen J, Herdewijn P.Screening a random pentapeptide library, composed of fourteen D-amino acids,

against the COOH-terminal sequence of fructose-1,6-biphosphate aldolase fromTrypanosoma brucei, J. Biol. Chem. 1997; 272:11378-11383.

Schraml J, van Halbeek H, De Bruyn A, Contreras R, Maras M, Herdewijn P.Hadamard 1D 1H TOCSY and its application to oligosaccharides, Magn. ResonanceChem. 1997; 35:883-888.

Polak M, Doboszewski B, Herdewijn P, Plavec J, Conformational studies on 2Z,3Z-unsaturated pentopyranosyl nucleosides by 1H NMR spectroscopy. Impact of π Sσ* interactions on the axial preference of the purine vs pyrimidine nucleobase, J.Am. Chem. Soc. 1997; 119:9782-9792.

Maurinsh Y, Schraml J, De Winter H, Blaton N, Peeters O, Lescrinier E, RozenskiJ, Van Aerschot A, De Clercq E, Busson R, Herdewijn P. Synthesis andconformational study of 3-hydroxy-4-(hydroxymethyl)-1-cyclohexanyl purines andpyrimidines, J. Org. Chem. 1997; 62:2861-2871.

Hendrix C, Rosemeyer H, De Bouvere B, Van Aerschot A, Seela F, Herdewijn P.1Z,5Z-Anhydrohexitol oligonucleotides: hybridization and strand displacement witholigoribonucleotides, interaction with RNase H and HIV-reverse transcriptase,Chemistry Eur. J. 1997; 3:1513-1520.

De Bouvere B, Kerremans L, Rozenski J, Janssen G, Van Aerschot A, Claes P,Busson R, Herdewijn P. Improved synthesis of anhydrohexitol building blocks foroligonucleotide synthesis, Liebigs Annalen Recl. 1997; 1453-1461.

Mikhailov S, Rodionov A, Efimtseva E, Fomitcheva, M, Padyukova N, Herdewijn P,Oivanen M, Preparation of pyrimidine 5Z-O-β-D-ribofuranosyl nucleosides. Hydrolyticstability of O-D-ribofuranosyl nucleosides, Carbohydrate Letters 1997; 2: 321-328.

Herdewijn P. Structural requirements for antiviral activity in nucleosides, DrugDiscovery Today 1997; 2:235-242.

Van Calenbergh S, Herdewijn P. Rational development of new sleeping sicknessdrugs, Current Medicinal Chemistry 1997; 4:359-384.

Van Calenbergh S, von Frijtage Drabbe Künzel J, Blaton N, Peeters O, Rozenski J,Van Aerschot A, De Bruyn A, De Keukeleire D, IJzerman A, Herdewijn P. N6-Cyclopentyl-3Z-substituted xylofuranosyl adenosines: a new class of non-xanthineadenosine A1 receptor antagonists, J. Med. Chem. 1997; 40:3765-3772.

Ceulemans G, Van Aerschot A, Wroblowski B, Rozenski J, Hendrix C, HerdewijnP. Oligonucleotide analogues with 4-hydroxy-N-acetylprolinol as sugar substitute,Chemistry Eur. J. 1997; 3:1997-2010.

Busson R, Schraml J, Saeyens W, Van der Eycken E, Herdewijn P, De KeukeleireD, Ortho photocycloaddition of substituted 4-phenoxybut-1-enes. Identification ofrearranged photocycloadducts by NMR, Bull. Soc. Chim. Belg. 1997; 106:671-676.

Marangoni M, Van Aerschot A, Augustyns P, Rozenski J, Herdewijn P. Synthesisand hybridization properties of inverse oligonucleotides, Nucleic Acids Res. 1997;23:3034-3041.

Ceulemans G, Van Aerschot A, Rozenski J, Herdewijn P. Oligonucleotides with 3-hydroxy-N-acetylprolinol as sugar substitute, Tetrahedron 1997; 53:14957-14974.

Croes K, Casteels M, Asselberghs S, Herdewijn P, Mannaerts G, P. Van Veldhoven,Formation of a 2-methyl branched fatty aldehyde during peroxisomal α-oxidation,FEBS Letters 1997; 412:643-645.

Rozenski J, Meier C, Aubagnac J.-L, Astier R, Herdewijn P, Imbach J.-L, GosselinG, Fast-atom bombardment mass spectrometric study of SATE Foscarnet prodrugsand of a series of Foscarnet-AZT conjugates, Rapid Communic. Mass Spectrom.1997; 11:1212-1218.

Wouters J, Creuven I, Norberg B, Evrard G, Durant F, Van Aerschot A, HerdewijnP. Trans- and cis-S-C-C-S conformations in 5-(2,2Z-dithien-5-yl)-2Z-deoxyuridine,Acta Cryst. 1997; C53:892-895.

1998

Basnak I, Sun M, Hamor TA, Focher F, Verri A, Spadari S, Wroblowski B,Herdewijn P, Walker RT, Some 6-aza-5-substituted-2Z-deoxyuridines show potentand selective inhibition of herpes simplex virus type 1 thymidine kinase,Nucleosides Nucleotides 1998; 17:187-206.

Link A, Lescrinier T, Kerremans L, Rozenski J, Herdewijn P. Side reactions in solidphase peptide synthesis caused by sulfonyl-ornithine building blocks, Die Pharmazie1998; 53:200-201.

Wang J, Busson R, Blaton N, Rozenski J, Herdewijn P. Enantioselective approachto the synthesis of cyclohexane carbocyclic nucleosides, J. Org. Chem. 1998;63:3051-3058.

Hossain N, van Halbeek H, De Clercq E, Herdewijn P. Synthesis of 3Z-C-branched1Z,5Z-anhydromannitol nucleosides as new antiherpes agents, Tetrahedron 1998;54, 2209-2226.

Lescrinier T, Hendrix C, Kerremans L, Rozenski J, Link A, Samyn B, Van AerschotA, Lescrinier E, Van Beeumen J, Herdewijn P. Peptide based DNA-binding ligandsusing combinatorial chemistry, Chemistry, European Journal 1998; 4, 425-433.

Hossain N, Herdewijn P. Facile synthesis of 3Z-C-branched 1,5-anhydrohexitolnucleosides, Nucleosides Nucleotides 1998; 17:1781-1786.

Hossain N, Herdewijn P. Synthesis of 1,5-anhydro-D-mannitol nucleosides with apurine base moiety, Nucleosides Nucleotides 1998; 17:1775-1779.

Efimtseva EV, Victorova LS, Rodionov AA, Ermolinsky BS, Formitcheva MV,Tunitskaya,VL, Mikhailov SN, Oivanen M, Van Aerschot A, Herdewijn P.Disaccharide nucleosides and their enzymatic and chemical incorporation intooligonucleotides, Nucleosides Nucleotides 1998; 17:1681-1684.

Luyten I, Herdewijn P. Hybridization properties of base modified oligonucleotideswithin the double- and triple helix motif, Eur. J. Med. Chem., 1998; 33:515-576.

Allart B, Van Aerschot A, Herdewijn P. 1,5-Anhydro-2-deoxy-D-altritololigonucleotides as conformationally restricted analogues of RNA, NucleosidesNucleotides 1998; 17:1523-1526.

Turner S, Herdewijn P. Synthetic strategies towards the synthesis of 1-(2,4-dideoxy-4-C-hydroxymethyl-α-L-lyxopyranosyl)base nucleosides, NucleosidesNucleotides 1998; 17:2085-2086.

Ceulemans G, Van Aerschot A, Herdewijn P. Divers stereoisomers of N-acetylhydroxylprolinol as sugar substitute in oligonucleotides, NucleosidesNucleotides 1998; 17:1577-1581.

Van Calenbergh S, IJzerman A, Herdewijn P. 3Z-Amidated 3Z-deoxyxylofuranoseanalogues of N6-cyclopentyladenosine: a new class of non-xanthine antagonists atthe adenosine A1 receptor, Nucleosides Nucleotides 1998; 17:1571-1576.

Schraml J, Kvicalova M, Blechta V, Rericha R, Rozenski J, Herdewijn P. 29Si NMRspectra of trimethylsilyl and tert-butyldimethylsilyl derivatives of purines andpyrimidines, Magn. Resonance Res. 1998; 36:55-63.

Hossain N, Wroblowski B, Van Aerschot A, Rozenski J, De Bruyn A, Herdewijn P.Oligonucleotides composed of 2Z-deoxy-1Z,5Z-anhydro-D-mannitol nucleosides witha purine base moiety, J. Org. Chem. 1998; 63, 1574-1582.

Champness J.-N, Bennett MS, Wien F, Visse R, Summers WC, Herdewijn P, DeClercq E, Ostrowski T, Jarvest RL, Sanderson MR, Exploring the active site ofherpes simplex virus type-1 thymidine kinase by X-ray crystallography ofcomplexes with aciclovir and other ligands, Proteins, Struct. Func., Genetics 1998;31:350-361.

Ostrowski T, Wroblowski B, Busson R, Rozenski J, De Clercq E, Bennett M,Champness J, Summers W, Sanderson M, Herdewijn P. 5-Substituted pyrimidineswith an 1,5-anhydro-2,3-dideoxy-D-arabino-hexitol moiety at N-1: synthesis,

antiviral activity, conformational analysis and interaction with viral thymidinekinase, J. Med. Chem. 1998; 41:4343-4353.

De Winter H, Lescrinier E, Van Aerschot A, Herdewijn P. Molecular dynamicssimulation to investigate differences in minor groove hydration of HNA/RNA hybridsas compared to HNA/DNA complexes, J. Am. Chem. Soc. 1998; 120:5381-5394.

Link A, Van Calenbergh S, Herdewijn P. Practical methodology for the parallelsynthesis of 2'-amido-2'-deoxyadenosines, Tetrahedron Lett., 1998; 39:5175-5176.

Mikhailov S, Rodionov A, Efimtseva E, Ermolinski B, Fomitcheva, M, Padyukova N,Rothenbacher K, Lescrinier E, Herdewijn P. Formation of trisaccharide nucleosideduring disaccharide nucleoside synthesis, Eur. J. Org. Chem., 1998:2193-2199.

Khan K, Van Schepdael A, Saison-Behmoaras T, Van Aerschot A, Hoogmartens J,Analysis of antisense oligonucleotides by on-capillary isotachophoresis and capillarypolymer sieving electrophoresis, Electrophoresis, 1988; 19:2163-2168.

1999

Lescrinier E, Sheng S, Schraml J, Busson R, Herdewijn P. d(GCGTAGC), anequilibrium between a hairpin structure and an unusual duplex, NucleosidesNucleotides, 1999; 18:2721-2744.

Lescrinier T, Hendrix C, Herdewijn P. Investigation on sarcosine and isonipecoticacid containing peptide nucleic acids, Nucleosides Nucleotides, 1999; 18:1535-1538.

Declercq R, Van Aerschot A, Herdewijn P, Van Meervelt L, Oligonucleotides with1,5-anhydrohexitol nucleoside building blocks. Crystallization and preliminary X-raystudies of h(GTGTACAC), Acta Cryst D., 1999; 55:279-280.

Maras M, De Bruyn A, Vervecken W, Uusitalo J, Penttila M, Busson R, HerdewijnP, Contreras R, In vivo synthesis of complex N-glycans by expression of human N-acetylglucosaminyltransferase I in the filamentous fungus Trichoderma reesei, FEBSLetters, 1999; 452:365-370.

Hossain N, Luyten I, Rothenbacher K, Busson R, Herdewijn P. Synthesis andconformational analysis of 1,5-anhydro-2,4-dideoxy-D-mannitol nucleoside,Nucleosides Nucleotides , 1999; 18:161-180.

Van Aerschot A, Maurinsh Y, Allart B, Boudou V, Herdewijn P. Analogues of hexitolnucleic acids: SFR of a new steric blocking agent, Coll. Czech. Chem. Commun.,1999; 2:100-104.

Thoithi G, Van Schepdael A, Vinckier C, Herdewijn P, Roets E, Hoogmartens J,Evaluation of the kinetics of hydrolysis of diamino analogues of 2Z- or 3Z-deoxy-adenosine and of 9-(2-deoxy-β-D-threo-pentofuranosyl)adenine or 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine by liquid chromatography, Nucleosides Nucleotides,1999; 18:1863-1877.

Mikhailov S, Rodionov A, E. Efimtseva, Ermolinski B, Fomitcheva, M, PadyukovaN, Rothenbacher K., Lescrinier E, Herdewijn P. Studies on disaccaride nucleosidesynthesis mechanism of the formation of trisaccacharide purine nucleosides,Nucleosides Nucleotides, 1999; 18:691-692.

Mikhailov S, Ermolinski B, E. Efimtseva, M. Brevnov, Gritsenko O, E. Gromova, VanAerschot A, Herdewijn P. Oligonucleotides with reactive dialdehyde groups as novelaffinity reagents, Nucleosides Nucleotides, 1999; 18:1469-1470.

Boudou V, Kerremans L, De Bouvere B, Lescrinier E, Schepers G, Busson R, VanAerschot A, Herdewijn P. Base-pairing of anhydrohexitol nucleosides with 2,6-diaminopurine 5-methylcytosine and uracil as base moiety, Nucleic Acids Res.,1999; 27:1450-1456.

Van Calenbergh S, Link A, De Keukeleire D, Herdewijn P. Lead optimization of N6-cyclopentyl-3'-amino-3'-deoxy-xylofuranolysadenines as adenosine A1 receptorantagonist, Nucleosides Nucleotides, 1999; 18:735-736.

Wang J, Herdewijn P. Enantioselective synthesis and conformational analysis ofcyclohexene carbocyclic nucleosides. Nucleosides Nucleotides, 1999; 18, 593-594.

Van Aerschot A, Vandermeeren M, Geysen J, Luyten I, Miller M, Atkins D, PreveralS, Saison E, Herdewijn P. In vitro evaluation of hexitol nucleic acid antisenseoligonucleotides, Coll. Czech Chem. Commun., 1999; 2:151-155.

Vastmans K, Kerremans L, Hendrix C, Van Aerschot A, Marliere P, Pochet S,Herdewijn P. Recognition of 1,5-anhydrohexitol adenine triphosphate by a DNApolymerase, Coll. Czech Chem. Commun., 1999; 2:156-160.

Boudou V, Rothenbacher K, Van Aerschot A, Herdewijn P. Oligonucleotide with2,6-diaminopurine base replacing for adenine: synthesis and properties, NucleosidesNucleotides, 1999; 18:1429-1431.

Busson R, Kerremans L, Van Aerschot A, Peeters M, Blaton N, Herdewijn P.

Unexpected shift to a 4-imino tautomer upon N4 acylation of 5-methylcytosin-1-yl

nucleoside analogues, Nucleosides Nucleotides, 1999; 18, 1079-1082.

Kozlov IA, Politis PK, Pitsch S, Herdewijn P, Orgel LE. A highly enantio-selectivehexitol nucleic acid template for non-enzymatic oligoguanylate synthesis. J. Am.Chem. Soc., 1999; 121:1108-1109.

Van Overmeire I, Boldin S, Dumont F, Van Calenbergh S, Slegers G, De KeukeleireD, Futerman AH, Herdewijn P. Effect of aromatic short-chain analogues onceramide on axonal growth in hippocampal neurons, J. Med. Chem., 1999;42:2697-2705.

Kozlov IA, Politis PK, Pitsch, S, Van Aerschot A, Busson R, Herdewijn P, Orgel LE,Non-enzymatic synthesis of RNA and DNA oligomers on hexitol nucleic acidtemplates: the importance of the A structure, J. Am. Chem. Soc., 1999;121:2653-2656.

Synthesis and pairing properties of oligonucleotides containing 3-hydroxy-4-hydroxymethyl-1-cyclohexanyl nucleosides. Maurinsh Y, Rosemeyer H, Esnouf R,A Medvedovici, Wang J, Ceulemans G, Lescrinier E, Hendrix C, Busson R, SeelaF, Sandra P, Van Aerschot A, Herdewijn P. Chem. Eur. J., 1999; 5:2139-2150.

Allart B, Khan K, Rosemeyer H, Schepers G, Hendrix C, Rothenbacher K, Seela F,Van Aerschot A, Herdewijn P. D-Altritol Nucleic Acids (ANA): HybridizationProperties, Stability and Initial Structural Analysis, Chemistry Eur. J., 1999;5:2424-2431.

Herdewijn P, Allart B, De Bouvere B, De Winter H, Hendrix C, Hossain N, SchepersG, Verheggen I, Wroblowski B, Van Aerschot A, Properties of oligonucleotides withsix membered carbohydrate mimics and a 1,4-relationship between the base moietyand the hydroxymethyl group, Nucleosides Nucleotides, 1999; 18:1371-1376.

Tunitskaya V, Rusakova E, Memelova L, Kochetkov S, Van Aerschot A, HerdewijnP, Efimtseva E, Ermolinski B, Mikhailov S, Mapping of T7 RNA polymerase activesite with novel reagents: oligonucleotides with reactive dialdehyde groups, FEBSLetters, 1999; 442:20-24.

Wang J, Herdewijn P. A novel and enantioselective approach to the synthesis ofcyclohexane carbocyclic nucleosides starting from (-)-carvone, NucleosidesNucleotides, 1999; 18:591-592.

Allart B, Busson R, Rozenski J, Van Aerschot A, Herdewijn P. Synthesis ofprotected D-altritol nucleosides as building blocks for oligonucleotide synthesis,Tetrahedron, 1999; 55:6527-6546.

Wouters J, Herdewijn P. 5-substituted pyrimidine 1,5-anhydrohexitol nucleosides:Conformational analysis and interaction with viral thymidine kinase, Bioorg. Med.Chem. Lett., 1999; 9:1563-1566.

Pochet S, Van Aerschot A, Herdewijn P, Marliere P. Replicative capability ofanhydrohexitol analogues of nucleotides, Nucleosides Nucleotides, 1999; 18:1015-1017.

Kozlov I, De Bouvere B, Van Aerschot A, Herdewijn P, Orgel L, Efficient transferof information from hexitol nucleic acids to RNA during non-enzymaticoligomerization, J. Am. Chem. Soc., 1999; 121:5856-5859.

Nandanan E, Camaioni E, Yang S.-Y, Kim Y.-C, Cristalli G, Herdewijn P, Secrist JA,Tiwari N, Mohanram A, Harden TK, Boyer JL, Jacobson KA, Structure-activityrelationship of bisphosphate nucleotide derivatives as P2Y1 receptor antagonistsand partial agonists, J. Med. Chem., 1999; 42, 1625-1638.

Raskin D, Smits I, Schepers G, Van Aerschot A, Augustijn P, Herdewijn P.Synthesis of 3Z- and 5Z-cholesterol conjugates of oligonucleotides for improvedcellular uptake, Coll. Czech Chem. Commun., 1999; 2:310-312.

Efimtseva EV, Rodionov A, Bobkov GV, Ermolinsky BS, Fomitcheva MV, MikhailovSN, Herdewijn P. Studies on disaccharide nucleoside synthesis, Coll. Czech Chem.Commun., 1999; 2:22-26.

Mikhailov SN, Ermolinsky BS, Efimtseva EV, Moiseyev GP, Tunitskaya VL,Rusakova EE, Kochetkov SN, Gritsenko OM, Gromova ES, Van Aerschot A,Herdewijn P. Oligonucleotides containing hexapyranosyl nucleosides anddisaccharide nucleosides: synthesis, incorporation of dialdehyde groups and use asaffinity reagents, Coll. Czech Chem. Commun., 1999; 2:141-144.

Van Calenbergh S, Link A, Fujikawa S, Vanheusden V, De Keukeleire D, YzermanAP. Herdewijn P. 5Z-deoxy congeners of 9-(3-amido-3-deoxy-β-D-xylofuranosyl)-N6-cyclopentyladenine: new adenosine A1 receptor antagonists, Coll. Czech Chem.Commun., 1999; 2:273-276.

De Jonghe S, Van Overmeire I, Poulton S, Hendrix C, Busson R, Van CalenberghS, De Keukeleire D, Spiegel S, Herdewijn P. Structure-activity relationship of short-chain sphingoid bases as inhibitors of sphingosine kinase, Bioorg. Med. Chem.Lett., 1999; 9:3175-3180.

Wang J, Herdewijn P. Enantioselective synthesis and conformational study ofcyclohexene carbocyclic nucleosides, J. Org. Chem., 1999; 64, 7820-7827.

Flores M, Atkins D, Stewart T, Van Aerschot A, Herdewijn P. Antimalarialantisense activity of hexitol nucleic acids, Parasitology Res., 1999; 85:864-866.

Dejonghe S, Van Overmeire F, Gunst J, De Bruyn A, Hendrix C, Van CalenberghS, Busson R, De Keukeleire D, Philippe J, Herdewijn P. Synthesis and apoptogenicactivity of fluorinated ceramide and dihydroceramide analogues, Bioorg. Med.Chem.Lett., 1999; 9:3159-3164.

Van Calenbergh S, Link A, Kunick C, Herdewijn P. Exploration of the effect ofsterically demanding 3Z-amido substitution of 3Z-deoxyadenosines towards inhibitionof cyclin-dependent kinase-1, Die Pharmazie, 1999; 54:727-729.

Herdewijn P. Conformational and stereochemical analysis as starting point for thedesign of antiviral compounds, Internat. Antiviral News, 1999; 7:148-153.

Dias N, Dheur S, Nielsen P, Gryaznov S, Van Aerschot A, Herdewijn P, Hélène C,Saison-Behmoaras T, Antisense PNAs targeted to the codon region of Ha-ras mRNAform practically ireversible duplexes with mRNA and inhibit its translation, J. Mol.Biol. 1999; 294:403-416.

Herdewijn P. Conformationally restricted carbohydrate-modified nucleic acids andantisense technology, Biochem. Biophys. Acta, 1999; 1489, 167-179.

De Bruyn A, Van Calenbergh S, Schraml J, Busson R, Herdewijn P. Killing illusionsby QUIET-NOESY, The NMR Newsletter, 1999; 491, 2-4.

Maes M, Orye K, De Bruyn A, Devreese B, van Beeumen J, Busson R, HerdewijnP, Messens E, Typing of the EPS coat of Erwinia amylovora strains in relation totheir phytopathological properties, Acta Horticulturae, 1999; 489, 337-340.

Dheur S, Dias N, Van Aerschot A, Herdewijn P, Bettinger T, Rémy J.-S, Hélène C,Saison-Behmoaras E, Polyethylenimine but not cationic lipid improves antisenseactivity of 3Z-capped phosphodiester oligonucleotides, Antisense and Nucleic AcidDrug Development, 1999; 9:515-525.

de Groot T., Bormans TJ, Busson R, Mortelmans L, Verbruggen A, Synthesis of 1-[18F]fluorodeoxyglucose: an unexpected rearrangement in the reaction of 2-O-methanosulfonyl-β-D-mannopyranose with [18F]fluoride, J. Labelled Cpd.Radiopharm, 1999; 42:147-157.

Dezutter NA, de Groot TJ, Busson R, Janssen GA, Verbruggen AM, Preparation of99mTc-N2S2 conjugates of chrysamine G, potential probes for the beta-amyloidprotein of Alzheimer's disease, J. Labelled Cpd. Radiopharm, 1999; 42:309-324.

2000

Boudou V, Longridge J, Van Aerschot A, Hendrix C, Millar A, Weiss P, HerdewijnP. Synthesis of the anticodon hairpin tRNAF

Met containing N[9-(β-D-ribofuranosyl)-purin-6-yl-carbamoyl]threonine (t6A), Helv. Chim. Acta., 2000; 83:152-161.

Nandanan E, Jang S.-Y, Moro S, Kim H, Siddique MA, Russ P, Marquez VE, BussonR, Herdewijn P, Harden TK, Boyer JL, Jacobson KA, Synthesis, biological activity,and molecular modeling of ribose-modified deoxyadenosine biphosphate analoguesas P2Y1 receptor ligands, J. Med. Chem., 2000; 43:829-842.

Vandermeeren M, Preveral S, Janssens S, Geysen J, Saison-Behmoaras E, VanAerschot A, Herdewijn P. Biological activity of hexitol nucleic acids targeted at Ha-ras and ICAM-1 mRNA, Biochem. Pharmacol., 2000; 59:655-663.

Kozlov I, Zielinski M, Allart B, Kerremans L, Van Aerschot A, Busson R, HerdewijnP, Orgel LE, Nonenzymatic template-directed reactions on altritol oligomers, pre-organized analogues of oligonucleotides, Chemistry, Eur. J., 2000; 6:151-155.

Van Calenbergh S, Herdewijn P. A heterogeneous collection of novel antiviralpyrimidines, Exp. Opin. Ther. Patents, 2000; 10:289-295.

Pierra C, Imbach J.-L, De Clercq E, Balzarini J, Van Aerschot A, Herdewijn P, FaraqA, Loi AG, Somadossi JP, Gosselin G, Synthesis and antiviral evaluation of someβ-L-2Z,3Z-dideoxy-5-chloropyrimidine nucleosides and pronucleotides, AntiviralResearch, 2000; 45:169-183.

Wang J, Froeyen M, Hendrix C, Andrei G, Snoeck R, De Clercq E, Herdewijn P. Thecyclohexene ring system as a furanose mimic: synthesis and antiviral activity ofboth enantiomers of cyclohexenyl G, J. Med. Chem., 2000; 43:736-745.

Thoithi G, Van Schepdael A, Busson R, Janssen G, Van Aerschot A, Herdewijn P,Roets E, Hoogmartens J, Investigation of the kinetics of degradation ofhexopyranosylated cytosine nucleosides using liquid chromatography, Nucleos.Nucleot. Nucleic Acids, 2000; 19:189-203.

Lagoja I, Van Aerschot A, Hendrix C, Herdewijn P. Glycosylation reaction of N-aminoimidazoline-2-thiones, Collect. Czech Chem. Commun., 2000; 65, 1145-1155.

De Bruyn A, Maes M, Busson R, Herdewijn P, Messens E, NMR experiments for theidentification of phytopathological features in the exo-polysaccharide amylovoran,The NMR Newsletter, 2000; 499:27-28.

Atkins D, Miller M, De Bouvere B, Van Aerschot A, Herdewijn P. Evaluation of thecellular uptake of hexitol nucleic acids in HeLa cells, Die Pharmazie, 2000; 55:615-617.

Wang J, Verbeure B, Luyten I, Lescrinier E, Froeyen M, Hendrix C, Rosemeyer H,Seela F, Van Aerschot A, Herdewijn P. Cyclohexene nucleic acids (CeNA): serumstable oligonucleotides that activate RNase H and increase duplex stability withcomplementary RNA, J. Am. Chem. Soc., 2000; 122:8595-8602.

Zhang Z, Van Aerschot A, Hendrix C, Busson R, Herdewijn P. Synthesis of alanineand proline amino acids with amino or guanidium substitution on the side chain,Tetrahedron, 2000; 56:2513-2522.

Froeyen M, Wroblowski B, Esnouf R, De Winter H, Allart B, Lescrinier E, HerdewijnP. Molecular dynamics studies of single-stranded hexitol, altritol, mannitol andribose nucleic acids (HNA, MNA, ANA, RNA) and of the stability of HNA:RNA;ANA:RNA and MNA:RNA duplexes, Helv. Chim. Acta, 2000; 83:2153-2182.

Luyten I, Esnouf R, Mikhailov S, Michiels P, Heus H, Hilbers C, Herdewijn P.Solution structure of a RNA decamer duplex, containing 9-[(2-O-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine, a special residue in lower Eukaryotic initiator tRNAs,Helv. Chim. Acta, 2000; 83:1278-1289.

Lescrinier E, Esnouf R, Schraml J, Busson R, Herdewijn P. Solution structure of ahexitol nucleic acid duplex with four consecutive T:T base pairs, Helv. Chim. Acta,2000; 83:1291-1310.

Van Overmeire I, Boldin S, Venkataraman K, Zisling R, De Jonghe S, VanCalenbergh S, De Keukeleire D, Futerman A, Herdewijn P. Synthesis and biologicalevaluation of ceramide analogues with substituted aromatic rings or an allylicfluoride in the sphingoid part, J. Med. Chem., 2000; 43:4189-4199.

Meyermans H, Morreel K, Lapierre C, Pollet B, De Bruyn A, Busson R, HerdewijnP, Devreese B, van Beeumen J, Marita J, Ralph J, Chen C, Burggraeve B, VanMontagu M, Messens E, Boerjan. W, Modifications in lignin and accumulation ofphenolic glucosides in poplar xylem upon downregulation of Caffeoyl-coenzyme AO- methyltransferase, an enzyme involved in lignin biosythesis, J. Biol. Chem.,2000; 275:36899-36909.

Herdewijn P. Heterocyclic modifications of oligonucleotides and antisensetechnology, Antisense and Nucleic Acid Drug Development, 2000; 10:297-310.

Lescrinier E, Esnouf R, Schraml J, Busson R, Heus HA, Hilbers CW, Herdewijn P.Solution structure of a HNA-RNA hybrid, Chemistry and Biology., 2000; 7:719-731.

Vastmans K, Pochet S, Peys A, Kerremans L, Van Aerschot A, Hendrix C, MarlièreP, Herdewijn P. Enzymatic incorporation in DNA of sugar-modified nucleotides,Biochemistry., 2000; 39:12757-12765.

De Jonghe S, Van Overmeire I, Van Calenbergh S, Hendrix C, Busson R, DeKeukeleire D, Herdewijn P. Synthesis of fluorinated sphinganine anddihydroceramide analogues, Eur. J. Org. Chem., 2000; 3177-3183.

Gritsenko OM, Mikhailov SN, Efimtseva E, Van Aerschot A, Herdewijn P, GromovaI, Probing the MUAI methyltransferase region that interacts with DNA: affinity

labeling with the dialdehyde-containing DNA duplexes, Nucleos. Nucleot. NucleicAcids, 2000; 19:1805-1820.

Rodionov A, Efimtseva EV, Mikhailov S, Rozenski J, Luyten I, Herdewijn P.Synthesis and properties of O-β-D-ribofuranosyl-(1]-2Z)-adenosine-5]-O-phosphateand its derivatives, Nucleos. Nucleot. Nucleic Acids, 2000; 19:1847-1851.

Wang J, Herdewijn P. A novel and enantioselective approach to the synthesis ofcyclohexane carbocyclic nucleosides starting from (-)-carvone, NucleosidesNucleotides, 2000; 18:591-592

Van Boven M, Busson R, Cokelaere M, Flo G, Decuypere E, 4-Demethylsimmondsin from Simmondsia chinensis, Ind. Crops Prod., 2000; 12:203-208.

Van den Mooter G, Wuyts M, Blaton N, Busson R, Grobet P, Augustijns P, KingetR, Physical stabilisation of amorphous ketoconazole in solid dispersions withpolyvinylpyrrolidone K25, Eur. J. Pharm. Sci., 2000; 12:261-269.

II. Mededelingen op internationale congressen en bijeenkomsten.

IIa. Integraal gepubliceerd in proceedings

1996

van Halbeek H, Schraml J, De Bruyn A, Contreras R, Maras M, Herdewijn P.Hadamard 1D 1H TOCSY of oligosaccharides, in Proc. 24th Annual Meeting of theSociety for Glycobiology, Boston, Massachusetts, U.S.A., 23-26 November 1996.,Glycobiology 1996, 6:734.

Sanderson MR, Bennett M, Champness JN, Wien F, Visse R, De Clercq E,Herdewijn P, Ostrowski T, Summers WC, X-ray structural study to 2.2Ä resolutionof herpes simplex thymidine kinase in complex with deoxythymidine and a rangeof nucleoside analogues, in Proc. 2nd European Biophysics Congress, Orleans,France, 13-17 July 1997, Eur. Biophys. J. 1997, 26:15.

IIb. Niet gepubliceerd of slechts beschikbaar als abstract

1996

26-30 January, HPCE 97, Anaheim, California, U.S.A., Khan K, Van Schepdael A,Van Aerschot A, Herdewijn P, Lemière F, Esmans E, Hoogmartens J, Applicationof capillary electrophoresis in monitoring the iodination reaction of anoligonucleotide.

17-20 March, Modified nucleic acids : chemistry and applications, Banbury Center,Cold Spring Harbor Laboratory, NY, U.S.A., Herdewijn P. Backbone modificationsresulting in strong hybridizing oligonucleotides

15 March, McGill University, Dept. Chemistry, Montreal, Canada, Herdewijn P.Hexitol Nucleic Acids.

17-19 April, VIIth International Symposium on Luminescence Spectrometry inBiomedical Analysis, Nice, France, Saeyers W, De Keukeleire D, Herdewijn P, DeBruyn. A Access to sterically confined nucleoside analogues via intra-molecularphotocycloadditions of arene-alkene trichromophores

12-16 May, Portland (Oregon), USA, 44th ASMS Conference on MassSpectrometry. Rozenski J, Hossain N, Herdewijn P. High-energy collision-induceddissociation of homo-N-deoxynucleosides.

19-24 May, 13th European Experimental NMR Conference, Paris, France, De BruynA, Maras M, Schraml J, Herdewijn P, Fiers W, Contreras R, Use of NMR inengineering of the carbohydrate moiety of fungal glycoproteins to a mammaliantype.

9-12 June, International Congres on Therapeutic Oligonucleotides, Rome, Italy,Hendrix C, De Bouvere B, Kerremans L, De Winter H, Herdewijn P, Van AerschotA, Hexitol nucleic acids (HNA) : a perfect partner for RNA.

7-10 July, Churchill College, Cambridge, U.K., Recent advances in the chemistryof anti-infective agents, Herdewijn P. Nucleosides with a six memberedcarbohydrate moiety, structural requirements for antiviral activity.

17-19 July, 2nd EuroConference on Carbohydrate Mimics, Lago di Garda, Italy,Herdewijn P. Oligonucleotides with a anhydrohexitol phosphate backbone.

1-6 September, XIth Int. Symp. Organosilicon Chem., Montpellier, France, SchramlJ, Kvicalova M, Blechta V, Cermak J, Herdewijn P. Tert-Butyldimethylsilyl 29Si NMRtag.

1-7 September, X Symposium on the Chemistry of Nucleic Acid Components, TrestCastle, Tsjechië, Ceulemans G, Herdewijn P. Nucleosides and oligonucleotidesderived from trans-4-hydroxy-N-acetyl prolinol.

1-7 September, X Symposium on the Chemistry of Nucleic Acid Components, TrestCastle, Tsjechië, Marangoni, M. Van Aerschot A, Augustyns P, Herdewijn P.Cyclopenthylethyl nucleosides as ^constrained] acyclic building blocks foroligonucleotides.

1-7 September, X Symposium on the chemistry of Nucleic Acid Components. TrestCastle, Tsjechië, Efimtseva E, Ermolinski B, Fomicheva M, Mikhailov S, HerdewijnP. Synthesis of disaccharide nucleosides and their incorporation intooligonucleotides.

1-7 September, X Symposium on the chemistry of Nucleic Acid Components. TrestCastle, Tsjechië, Mikhailov S, Ermolinksy B, Efimtseva E, Van Aerschot A,Herdewijn P. Regioselective incorporation of reactive dialdehyd groups intosynthetic oligonucleotides.

8-12 September, Maastricht, The Netherlands, XIVth International Symposium onMedicinal Chemistry, Herdewijn P. Antisense oligonucleotides.

8-12 September, XIVth Internat. Symp. Medicinal Chemistry, Maastricht, TheNetherlands, Maurinsh Y, Blaton N, Herdewijn P. Cyclohexanyl nucleosides :synthesis of 3-hydroxy-4-hydroxymethyl-1-cyclohexanyl purines and pyrimidines.

8-12 September, XIVth Int. Symposium Medicinal Chemistry, Maastricht, TheNetherlands, Herdewijn P. Antiviral Agents, review Current Drugs.

13 September, Glaxo Wellcome, Research Triangle Park, NC, U.S.A., Herdewijn P.Anhydrohexitol as furanose mimics.

15-19 September, 12th Int. Round Table Nucl. Nucl., La Jolla, California, U.S.A.,Luyten I, Van Aerschot A, Rozenski J, Busson R, Herdewijn P. Protection of 2,6-diaminopurine deoxyriboside.

15-19 September, 12th Int. Round Table Nucl. Nucl., La Jolla, California, USA, VanAerschot A, De Bouvere B, Hendrix C, Kerremans L, De Winter H, Herdewijn P.Hexitol nucleic acids: synthesis and properties.

28 September, 1st Minisymposium on Therapeutic potentialities of 3Z-end modifiedantisense oligonucleotides targeted to codon 12 mutated Ha-ras, Paris, France,Herdewijn P, Hendrix C, Van Aerschot A, Synthesis and properties of 3Z-modifiedoligonucleotides.

8 November, 27th Microsymposium on Glycosomes, Heidelberg, Germany, SamsonI, Herdewijn P. Peptide libraries for de novo lead identification against trypanosomabrucei.

1997

28 January, Johan Wolfgang Goethe-University, Frankfurt, Germany, Herdewijn P.,Development of hexitol nucleic acids.

18-19 February, Intern. Symp. Advances in NMR, Johannes Kepler University, Linz,Austria, Polak, M. Herdewijn P, Plavec J, Conformational characteristics ofunsaturated pentopyranosyl nucleosides studied by 1H NMR.

18-19 February, Intern. Symp. Advances in NMR, Johannes Kepler University, Linz,Austria, Schraml J, Van Halbeek H, De Bruyn A, Herdewijn P, Contreras R, MarasM,Hadamard 1-D-TOCSY.

23-27 March, 38th Experimental Nuclear Magnetic Resonance Conference,Orlando, Florida, USA, Van Halbeek H, Sheng S, Lescrinier E, De Bruyn A,Herdewijn P. Semi-selective F1-decoupled TOCSY recorded with pulsed fieldgradients.

6 April, ISAR pre-satellite symposium, Emory University, Altanta, Georgia, USA,Herdewijn P. Six-membered antiviral agents.

11 April, Ribozyme Pharmaceuticals Inc., Boulder, Colorado, USA, Herdewijn P.Conformationally constrained oligonucleotides.

1- 6 June, IVth International Symposium on Bioorganic Chemistry, Biarritz, France,Van Overmeire I, De Keukeleire D, Herdewijn P. Efficient and stereoselective accessto a ceramide-1-phosphate analogue.

6-8 June, 1st Minisymposium on Virosome-mediated Gene Therapy against HIV-1,Pavia, Italy, Herdewijn P. A chemical approach to target Tar-TAT interactions.

12 June, 2nd Minisymposium on therapeutic potentialities of 3Z-end modifiedantisense oligonucleotides targeted to codon 12 mutated Ha-ras, Paris, France,Hendrix C, Herdewijn P. Propanediol modified oligonucleotides: enzymatic stabilityvs biological activity.

12 June, 2nd Minisymposium on therapeutic potentialities of 3Z-end modifiedantisense oligonucleotides targeted to codon 12 mutated Ha-ras, Paris, France, VanAerschot A, Marangoni M, Herdewijn P. Ceramide modified oligonucleotides.

29 June-4 July, Gorden Conference on Purine, Pyrimidine and Related Substances,Salve Regina, New Port, USA, Herdewijn P. Rational and irrational design of newnucleoside and nucleotide structures of biological relevance.

29 June-4 July, Gorden Conference on Purine, Pyrimidine and Related Substance,Salve Regina, New Port, USA, Basnak I, Hamor T, Focher F, Verri A, Spadari S,Wroblowski B, Herdewijn P, Walker R, Some 6-aza-5-substituted-2Z-deoxyuridinesshow potent and selective inhibition of herpes simplex virus type 1 thymidinekinase.

6-11 July, 13th International Meeting on NMR Spectroscopy, University of Exeter,U.K., Sheng, S. Van Halbeek H, Schraml J, Herdewijn P. Semi-selective ω1-decoupled TOCSY recorded with pulsed field gradients.

6-11 July, 9th European Carbohydrate Symposium, Utrecht, Nederland, De BruynA, Schraml J, Maras M, Contreras R, Herdewijn P. NMR techniques in the study ofprotein-linked carbohydrates.

6-11 July, Eurocarb 9, Utrecht, The Netherlands, De Bruyn A, Schraml J, MarasM, Contreras R, Herdewijn P. NMR techniques in the study of protein linkedcarbohydrates.

17-21 August, EMBO Practical Course ^Multidimensional NMR in StructuralBiology], Il Ciocco, Lucca, Italy, Lescrinier E, van Halbeek H, De Bruyn A, BussonR, Herdewijn P. Structure determination of d(GCGTAGC): a temperature dependentequilibrium between a monoloop hairpin and a non-canonical duplex structure.

31 August-3 September, Hendrix C, Rosemeyer H, Van Aerschot A, Seela F,Herdewijn P. 4th Cambridge Symposium ^Oligonucleotide chemistry and biology],QueensZ College, Cambridge, U.K., Interaction of 1Z,5Z-anhydrohexitololigonucleotides with DNA, RNA and DNA:RNA binding enzymes.

31 August-3 September, Hendrix C, Rosemeyer H, Van Aerschot A, Seela F,Herdewijn P. 4th Cambridge Symposium ^Oligonucleotide chemistry and biology],QueensZ College, Cambridge, U.K., Verbeure B, Herdewijn P. Synthesis of aribozyme mimic.

31 August- 5 September, XII FECHEM Conference on Organometallic Chemistry,Prague, Schraml J, Kvicalova M, Blechta V, Rericha R, Herdewijn P. 29Si NMRspectra in the nucleoside synthesis via the organosilicon route.

4-9 September, International Conference on ^Nucleic Acids and RelatedMacromolecules: Synthesis, Structure and Applications, Ulm, Germany, Allart B,Wroblowski B, Van Aerschot A, Herdewijn P. 1,5-Anhydro-2-deoxy-D-altritololigonucleotides as conformationally restricted analogs of RNA.

4-9 September, International Conference on ^Nucleic Acids and RelatedMacromolecules: Synthesis, Structure and Applications, Ulm, Germany, CeulemansG, Van Aerschot A, Herdewijn P. Oligonucleotides with 4-hydroxy-N-acetylprolinolas sugar substitute.

4-9 September, International Conference on ^Nucleic Acids and RelatedMacromolecules: Synthesis, Structure and Applications, Ulm, Germany, Wang J,Herdewijn P. A novel and enantioselective approach to the synthesis ofcyclohexane carbocyclic nucleosides starting from (-)-carvone.

4-9 September, International Conference on ^Nucleic Acids and RelatedMacromolecules: Synthesis, Structure and Applications, Ulm, Germany, HossainN, Wroblowski B, Van Aerschot A, Herdewijn P. Facile synthesis of 1,5-anhydro-D-mannitol nucleosides, with a purine base moiety and incorporation intooligonucleotides.

4-9 September, International Conference on ^Nucleic Acids and RelatedMacromolecules: Synthesis, Structure and Applications, Ulm, Germany, Hossain

N, De Clercq E, Herdewijn P. Facile synthesis of 3Z-C-branched 1,5-anhydrohexitolnucleosides and their antiviral activities.

4-9 September, International Conference on ^Nucleic Acids and RelatedMacromolecules: Synthesis, Structure and Applications, Ulm, Germany, Turner SJ,Herdewijn P. Synthetic strategies towards the synthesis of 1-(2,4-dideoxy-4-C-hydroxymethyl-α-L-lyxopyranosyl)base nucleosides.

4-9 September, International Conference on ^Nucleic Acids and RelatedMacromolecules: Synthesis, Structure and Application], Ulm, Germany, VanCalenbergh S, IJzerman A, Herdewijn P. 3'-Amidated 3'-deoxyxylo-furanoseanalogues of N6-cyclopentyladenosines: a new class of non-xanthine antagonistsat the adenosine A1 receptor.

7-12 September, Glyco XIV Symposium, Zurich, Switzerland, van Halbeek H,Schraml J, De Bruyn A, Maras M, Contreras R, Herdewijn P. Novel techniques forNMR of oligosaccharides. Hadamard 1D 1H TOCSY.

15-19 September, Association of Swiss-French Universities, Champéry,Switzerland, Herdewijn P. Design of antisense oligonucleotides.

15-19 September, Association of Swiss-French Universities, Champéry,Switzerland, Herdewijn P. Peptide libraries for discovery of dsDNA binding ligands.

15-19 September, Association of Swiss-French Universities, Champéry,Switzerland, Herdewijn P. Quantitative and qualitative predictions of biologicalactivity of nucleosides.

2-5 October, Jahrestagung der deutschen und schweizerischen pharmazeutischenGesellschaften, Zurich, Switzerland, Lescrinier T, Hendrix C, Kerremans L, RozenskiJ, Link A, Van Aerschot A, Lescrinier E, Herdewijn P, Samyn B, Van Beeumen J,Kombinatorische Synthese von DNA-Liganden.

1998

5 March, Minisymposium on Medicinal Chemistry, Danish Chemical Society OrganicChemistry Section, Copenhagen, Denmark, Herdewijn P. Unnatural peptide librariesfor recognition of nucleic acids.

6 March, Kemisk Institut, University of Copenhagen, Copenhagen, Denmark,Herdewijn P. Hexitol based nucleosides and oligonucleotides.

5-9 April, NACON IV, Sheffield, UK, De Winter H, Lescrinier E, Van Aerschot A,Luyten I, Herdewijn P. Minor groove solvatation contributes to the relative stabilityof HNA/RNA hybrids as compared to HNA/DNA complexes.

5 May, Jubilee of 50 years International symposium on crop protection. Universityof Ghent, Maes M, Orye K, Crepel C, De Bruyn A, Devreese B, Busson M,Herdewijn P, Messens E, Influence of the capsular polysaccharides on the virulenceof Erwinia amylovora strains.

10-15 May, EENC 98 BLED, 14th European Experimental NMR Conference. Bled,Slovenia, De Bruyn A, Schraml J, Herdewijn P. The use of selective excitation inthe structure analysis of carbohydrates and nucleic acids.

17-22 May, 6th International Conference "AIDS, cancer and related problems", St.-Petersburg, Russia, Herdewijn P. Peptide libraries for the discovery of DNA-bindingligands.

28 May, Journées Franco-Belges, Université de Caen, Centre d'études et derecherche sur le médicament de Normandie, Caen, France, Herdewijn P. Etuded'oligonucleotides antisenses à structure hexitol.

28 June _ 3 July, Gordon Research Conferences "Computational Chemistry", TiltonSchool, Tilton NH, USA, Wroblowski B, Herdewijn P. Stability of 3'-hydroxy-hexitolnucleotide/RNA complexes studied by molecular dynamics simulation.

9-14 August, XIXth International Carbohydrate Symposium, San Diego, California,USA, Herdewijn P. Carbohydrate-containing ligands targeting nucleic acids.

23-28 August, XVIIIth International Conference on Magnetic Resonance inBiological Systems, Tokyo Metropolitan University, Hachioji, Tokyo, Japan, DeBruyn A, Maras M, Contreras R, Schraml J, Busson R, Van Calenbergh S,Herdewijn P. Application of selective excitation in structural assignment of highmannose type glycans.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Herdewijn P, Allart, B. De Bouvere B,De Winter H, Hendrix C, Hossain N, Schepers G, Verheggen I, Wroblowski B, VanAerschot A, An update of the present knowledge on hexitol nucleic acids.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Lescrinier T, Hendrix C, Rozenski J,Van Aerschot A, Herdewijn P. Peptide libraries containing unnatural amino acidsscreened for DNA-binding ligands.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Van Aerschot A, Vandermeeren M,Geysen J, Luyten W, Miller M, Atkins D, Preveral S, Saison-BehmoarasT, HerdewijnP. In vitro evaluation of hexitol nucleic acid (HNA) antisense oligonucleotides.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Allart B, Van Aerschot A, Schepers G,Herdewijn P. Physicochemical properties of altro-hexitol nucleic acids (ANA).

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Allart B, Van Aerschot A, HerdewijnP. Synthesis of 1,5-anhydro-2-deoxy-D-altritol building blocks for oligonucleotidesas conformationally restricted analogues of RNA.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Boudou V, Van Aerschot A, HerdewijnP. Oligonucleotides with the base 2,6-diaminopurine replacing for adenine:synthesis and properties.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Wang J, Herdewijn P. Enantioselectivesynthesis and conformational analysis of novel six-membered carbocyclicnucleosides.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Lescrinier E, Busson R, Heus HA,Hilbers CW, Herdewijn P. Structural determination of a RNA/HNA hybrid by NMRspectroscopy.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Van Calenbergh S, Link A, Ijzerman A,Herdewijn P. Lead optimization of N6-cyclopentyl-3Z-amido-3Z-deoxyxylofuranosyladenosines as adenosine A1 receptor antagonists using solidphase chemistry.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Pochet S, Van Aerschot A, HerdewijnP, Marlière P. Replicative capability of anhydrohexitol analogues of nucleotides.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Mikhailov SN, Ermolinsky BS,Efimtseva EV, Gromova ES, Van Aerschot A, Herdewijn P. Oligonucleotides withreactive dialdehyde groups as novel affinity reagents.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Mikhailov SN, Rodionov A, EfimtsevaEV, Ermolinsky BS, Fomitcheva MV, Padyukova NS, Rothenbacher K, Lescrinier E,Herdewijn P. Studies on dissacharide nucleoside synthesis. Mechanism of theformation of trisaccharide purine nucleosides.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Luyten I, Mikhailov S, Busson R, Heus

H, Hilbers C, Herdewijn P. Solution structure of a 9-[2-O-ß-D-ribofuranosyl)-ß- D-ribofuranosyl]adenine-substituted RNA decamer duplex.

6-10 September, XIII International Round Table ^Nucleosides, Nucleotides and theirBiological Applications. Montpellier, France, Busson R, Van Aerschot A, M. Peeters,Blaton N, Herdewijn P. Unexpected shift to a 4-imino tautomer upon N4-acylationof 5-methylcytosin-1-yl nucleoside analogues.

12-15 October, IWFB 98, 8th International Workshop on fire blight. Kusadasi,Turkey, Maes M, Orye K, De Bruyn A, Devreese B, Van Beeumen J, Busson M,Herdewijn P, Messens E, Typing of the eps coat of erwinia amylovora strains inrelation to their phytopathological properties.

21-23 October, "Speeding up Drug Discover", Fachgruppe Medizinale ChemieGDCh, Schliersee, Germany, Link A, Van Calenbergh S, Rozenski J, Van AerschotA, Herdewijn P. Solid phase assisted synthesis of 2'-amido-2'-deoxyadenosines.3 November, Pasteur Institute, Paris, France, Herdewijn P. Modelling and design ofinhibitors and substrates of kinases.

1999

28 February _ 5 March, 40th Experimental Nuclear Magnetic ResonanceConference, Orlando, Florida, USA, De Bruyn A, Schraml J, Busson R, HerdewijnP. The use of selective excitation in the structure analysis of carbohydrates andnucleic acids.

26-28 March, 1st COST D13 Symposium, Noordwijk, Nederland, Herdewijn P.Control of gene expression by antisense oligonucleotides and synthetic peptides

8 April, The Salk Institute for Biological Studies, San Diego, California, USA,Herdewijn P. HNA-new nucleic acid analogues.

10 April, Annual F.L. Suddath Bio Science Symposium, Georgia TechnologicalUniversity, Atlanta, Georgia, USA, Herdewijn P.

20 May, Montpellier, France, Herdewijn P. Targeting nucleic acids for drug design.June 21, Nucleic Acids Chemistry, International Ph.D Summer School, Kollekolle,Denmark, Herdewijn P. Conformationally restricted antisense oligonucleotides.

June 21, Nucleic Acids Chemistry, International Ph.D Summer School, Kollekolle,Denmark, Herdewijn P. Properties of hexitol-base nucleic acids.

4-9 July, The 4th International Engelhardt Conference on molecular biology,Moscow-St. Petersburg, Russia, Herdewijn P. Properties of hexitol nucleic acids.

11-16 July, 12th International Conference on the Origin of Life and 9th ISSOLMeeting, San Diego, California, USA, Kozlov I, Politis P, Pitsch S, De Bouvere B,

Busson R, Van Aerschot A, Herdewijn P, Orgel L, Study of non-enzymaticsyntheses of RNA and DNA on RNA, DNA and HNA templates.

31 August - 4 September, 6th SPS Symposium, York, United Kingdom, Chaltin P,Van Aerschot A, Hendrix C.; Busson R, Herdewijn P. Oligopeptide-libraries for thesequence specific recognition of nucleic acids.

31 August - 4 September, 6th SPS Symposium, York, United Kingdom, Zhang Z,Van Aerschot A, Hendrix C, Busson R, Herdewijn P. Constrained guanidinium aminoacids as ligands for HIV-1 TAAR RNA.

31 August - 4 September, 6th SPS Symposium, York, United Kingdom, VerbeureB, Herdewijn P. Development of a di-imidaozole based ribozyme mimic.

31 August - 4 September, 6th SPS Symposium, York, United Kingdom, Boudou V,Lagoja I, Van Aerschot A, Weiss, P. Herdewijn P. Synthesis of the anticodonhairpin RNA of tRNAF

Met containing N[9-β-D-ribofuranosyl)-purine-6-yl-carbamoyl]threonine (t6A).

4-9 September, XIth Symposium, Chemistry of Nucleic Acids Components,Spindleruv Mlyn, Czech Republic, Raskin D, Smits I, Schepers G, Van Aerschot A,Augustijn P, Herdewijn P. Synthesis of 3Z- and 5Z-cholesterol conjugates ofoligonucleotides for improving cellular uptake.

4-9 September, XIth Symposium, Chemistry of Nucleic Acids Components,Spindleruv Mlyn, Czech Republic, Efimtseva EV, Rodionov A, Bokkov GV,Ermolinsky BS, Fomitcheva MV, Mikhailov SN, Herdewijn P. Studies ondisaccharide nucleoside synthesis.

4-9 September, XIth Symposium, Chemistry of Nucleic Acids Components,Spindleruv Mlyn, Czech Republic, Mikhailov SN, Ermolinsky BS, Efimtseva EV,Moiseyev GP, Tunitskaya VL, Rusakova EE, Kochetkov SN, Gritsenko OM,Gromova ES, Van Aerschot A, Herdewijn P. Oligonucleotides containinghexapyranosyl nucleosides and disaccharide nucleosides: synthesis, incorporationof dialdehyde groups and use as affinity reagents.

4-9 September, XIth Symposium, Chemistry of Nucleic Acids Components,Spindleruv Mlyn, Czech Republic, Vastmans K, Kerremans L, Hendrix C, VanAerschot A, Pochet S, Marlière P, Herdewijn P.Recognition of 1,5-anhydrohexitol adenine triphosphate by a DNA polymerase.

4-9 September, XIth Symposium, Chemistry of Nucleic Acids Components,Spindleruv Mlyn, Czech Republic, Van Calenbergh S, Link A, Fuyikawa S,Vanheusden V, De Keukeleire D, Yzerman A, Herdewijn P. 5Z-deoxy congeners of9-(3-amido-3-deoxy-β-D-cylofuranoyl)-N6-cyclopentyladenine new adenosine A1receptor antagonists.

21 October, Institut de Chimie de Substances Naturelles CNRS, Gif-sur-Yvette,France, Herdewijn P. Hexitol nucleic acids.

26 November, Frontiers of Nucleic Acid Chemistry, Osnabruck, Germany,Herdewijn P. Cyclohexene ring system as furanose mimic

9-10 December, Royal Pharmaceutical Society of Great Britain, London, UnitedKingdom, Herdewijn P. Peptide libraries, Gene targeted therapeutic strategies.

2000

18-22 January, 8th International Symposium on Natural Product Chemistry, Karachi,Pakistan, Herdewijn P. Properties of nucleic acids with a six-memberedcarbohydrate moiety.

30 January _ 5 February, 5th International Symposium on Bioorganic Chemistry,Pune, India, Herdewijn P. Synthesis and properties of nucleosides with a six-membered carbohydrate moiety.

10-11 February, 4. Igler NMR Tage. Perspectives in NMR spectroscopy, Innsbruck,Austria, Lescrinier E, Schraml J, Busson R, Herdewijn P. Solution structure of ahexitol nucleic acid duplex with four consecutive T:T base pairs.

25 February, Roche Diagnostics, Penzberg, Germany, Herdewijn P. Modifiednucleosides for polymerization reactions.

25-28 March, 7th Ibn Sina International Conference on Pure and AppliedHeterocyclic Chemistry, Alexandria, Egypt, Herdewijn P. Interactions between DNAand synthetic peptides.

16-21April, 13th International Conference on Antiviral Research, Baltimore,Maryland, USA, Andrei G, Wang J, R. Snoeck, De Clercq E, Herdewijn P. Antiviralactivity of D- and L-enantiomers of cyclohexenyl guanine.

21 April, ISIS Pharmaceuticals, Carlsbad, California, USA, Herdewijn P.Cyclohexene nucleosides and oligonucleotides: structure and properties.

30 May _ 4 June, RNA 2000; 5th Annual Meeting of the RNA Society, Madison,Wisconsin, USA, Luyten I, Herdewijn P, Sattler M, Structure determination of theanticodon stem-loop hairpin of cytoplasmic initiator tRNAi

Met using NMRspectroscopy.

20-25 August, XIX International Conference on Magnetic Resonance in BiologicalSystems, Florence, Italy, De Bruyn A, Maes M, Orye K, Busson R, Herdewijn P,Messens E, NMR experiments for the identification of the phytopathologicalproperties in the exopolysaccharide amylovoran.

10-14 September, XIV International Roundtable, San Francisco, California, USA,Van Aerschot A, Meldgaard M, Volders F, Schepers G, Rozenski J, Herdewijn P.Methyl ether analogues of hexitol nucleic acids (HNA).

10-14 September, XIV International Roundtable, San Francisco, California, USA,Lagoja IM, Pochet S, Herdewijn P. A new approach to isotopically labelednucleosides.

10-14 September, XIV International Roundtable, San Francisco, California, USA,Wang J, Froeyen M, Hendrix C, Andrei, G, Snoeck R, Lescrinier E, De Clercq E,Herdewijn P. D- and L-Cyclohexenyl G, a new class of antiviral agents: synthesis,conformational analysis, molecular modeling, and biological activity.

10-14 September, XIV International Roundtable, San Francisco, California, USA,Wang J, Verbeure B, Luyten I, Froeyen M, Hendrix C, Rosemeyer H, Seela F, VanAerschot A, Herdewijn P. Cyclohexene nucleic acids (CeNA) form stable duplexeswith RNA and induce RNase H activity

10-14 September, XIV International Roundtable, San Francisco, California, USA,Herdewijn P, Froeyen M, Lescrinier E, Wang J, Vastmans K, Verbeure B, VanAerschot A, Nucleic acids with a six-membered carbohydrate mimic: from structureto function.

III. Mededelingen op andere congressen en bijeenkomsten

IIIa. Integraal gepubliceerd in proceedings

1996

Khan K, Van Schepdael A, Van Aerschot A, Herdewijn P, Hoogmartens J,Iodination reaction of deoxyuridine in an oligonucleotide as monitored by capillaryelectrophoresis, In: Proc. 6de Forum der Farmaceutische Wetenschappen,Blankenberge, Belgium, 3-4 May 1996., Journal de Pharmacie de Belgique 1996,51:112.

IIIb.Niet gepubliceerd of slechts beschikbaar als abstract.

1996

7 May, 26th Microsymposium on Glycosomes, ICP, Brussels, Belgium, Samson I,Herdewijn P. Screening of the carboxyl terminal region of fructose 1,6-biphosphatealdolase.

8-12 July, 6th Belgian Organic Synthesis Symposium, Gent, Belgium, Saeyers W,Herdewijn P, De Keukeleire D, Selectivity control in intramolecularphotocycloadditions of substituted arene-alkylene trichromophores.

8-12 July, 6th Belgian Organic Synthesis Symposium, Gent, Belgium, VanOvermeire I, De Keukeleire D, Herdewijn P. Stereoselective synthesis of ceramide-1-phosphates.

8-12 July, 6th Belgian Organic Synthesis Symposium, Gent, Belgium, VanCalenbergh S, De Bruyn A, De Keukeleire D, Herdewijn P. Synthesis of a ^splittednucleoside] via a 1,3-dipolar cycloaddition reaction.

13 September, BSMS Annual Meeting, Louvain-la-Neuve, Belgium, Rozenski J,Kerremans L, De Bouvere B, Hossain N, Van Aerschot A, Herdewijn P.Characterization of N1- and O2-coupled pyrimidine nucleosides using massspectrometry.

1997

ASMS, Rozenski J, Marangoni M, Van Aerschot A, Herdewijn P, W. Van Dongen,Esmans E, Sequencing of Synthetic Oligonucleotides using ElectrosprayIonization/Tandem Mass Spectrometry.

ASMS, Rozenski J, Allart B, Van Aerschot A, Herdewijn P. Structure Determinationof a Nucleoside Side Product using CID LSIMS.

22 februari, Koninklijke Academie voor Geneeskunde van België, Brussel, België,Herdewijn P. Medische en farmaceutische toepassingen voor dehoofdcomponentenanalyse (Prof. D. Massart).

24 april, Belgisch Genootschap voor Farmaceutische Wetenschappen,Blankenberge, België,.Lescrinier T, Link A, Kerremans L, Rozenski J, Van AerschotA, Herdewijn P. Isolation of new DNA-ligands using combinatorial chemistry.

18-19 June, 1e VIB Congress, Gent, Belgium, Maras, M. Laroy W, Saelens X,Martinet W, De Bruyn A, Schraml J, Herdewijn P, Claeyssens M, Contreras R,Engineering of the carbohydrate moiety of fungal glyco-proteins to a mammaliantype.

28 October, Louvain-La-Neuve, Belgium, Herdewijn P. Antisense oligonucleotides:chemistry and biological applications.

29-30 August, TRICEL 97 Conference on "Carbohydrates from T.reesei and othermicroorganisms", Gent, Belgium, De Bruyn A, Schraml J, van Halbeek H, Maras M,Contreras R, Herdewijn P. NMR techniques in the study of protein linkedcarbohydrates.

29-30 August, TRICEL 97 conference on ^Carbohydrases from Trichoderma reeseiand other microorganisms], Ghent, Belgium, Van Halbeek H, Schraml J, De BruynA, Contreras R, Maras M, Herdewijn P. Hadamard 1D 1H TOCSY of aphosphorylated oligosaccharide from cellobiohydrolase I of trichoderma reesei.

3 December, Weizmann Institute of Science, Lod, Israel, Herdewijn P. A chemicalapproach for the control of gene expression.

4-5 December, SIGMA-ALDRICH Organic Synthesis Symposium, De Haan, Belgium,Van Calenbergh S, De Keukeleire D, Herdewijn P. Sugar modified adenosineanalogues; synthesis; biological applictions and conformational analysis.

4-5 December, SIGMA-ALDRICH Organic Synthesis Symposium, De Haan, Belgium,De Jonghe S, Herdewijn P, De Keukeleire D, Synthesis of dihydroceramides.

4-5 December, SIGMA-ALDRICH Organic Synthesis Symposium, De Haan, Belgium,Van Overmeire I, De Keukeleire D, Van Veldhoven P, Herdewijn P. Synthesis ofsfingosine analogues and their influence on sfingosine kinase.

18 December, Innogenetics, Zwijnaerde, Belgium, Herdewijn P. Design of biologicalactive nucleosides and oligonucleotides.

1998

7 April, 4b Vlaams Jongeren Congres van de Chemie, K.U.Leuven, Leuven,Belgium, De Jonghe S, Herdewijn P, De Keukeleire D, Stereoselectieve synthesevan korte-keten dihydroceramiden.

5-9 July, 7th Belgian Organic Synthesis Symposium, Louvain-la-Neuve, Belgium, DeJonghe S, Herdewijn P, De Keukeleire D, Stereoselective synthesis of short-chainanalogues of natural dihydroceramides.

14-15 November, Symp. from Gene to Clinic (in honour of Prof. W. Fiers), Gent,Belgium, Maras M, Laroy W, Saelens X, Martinet W, De Bruyn A, Schraml J,Herdewijn P, Claeyssens M, Contreras R, Engineering of the carbohydrate moietyof fungal glycoproteins to a mammalian type.

3-4 December, 2nd Sigma-Aldrich Organic Synthesis Meeting, De Haan, Belgium,De Jonghe S, De Keukeleire D, Herdewijn P. Synthesis of fluorinateddihydroceramide analogues.

1999

8 February, Ecole de Pharamacie, U.C.L., Woluwé-Saint-Lambert, Belgium,Herdewijn P. Design of antisense-oligonucleotides.

8 February, Ecole de Pharamacie, U.C.L., Woluwé-Saint-Lambert, Belgium,Herdewijn P, Antisense oligonucleotides with antiviral and antitumoral activity.

8 February, Cours Pharmacologie Cellulaire et Moléculaire U.C.L., Ecole dePharmacie, Woluwé-Saint-Lambert, Belgium, Herdewijn P. Design of Antisense-oligonucleotide.

8 February, Cours Pharmacologie Cellulaire et Moléculaire U.C.L., Ecole dePharmacie, Woluwé-Saint-Lambert, Belgium, Herdewijn P. Antisenseoligonucleotides with antiviral and antitumoral activity.

17 March, Faculty of Chemistry, U.C.L., Louvain-la-Neuve Belgium, Herdewijn P.How to design an antisense experiment.

17 March, Faculty of Chemistry, U.C.L., Louvain-la-Neuve Belgium, Herdewijn P.Properties of hexitol nucleic acids.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, Vastmans K, PochetS, Kerremans L, Hendrix C, Van Aerschot A, Herdewijn P. Enzymatic recognitionof 1,5-anhydrohexitol nucleosides and oligonucleotides.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, J. De Haes,Herdewijn P. Pteridine-2,4-diones: a new class of immunosuppressive drugs.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, Smits I, Raskin D,Schepers G, Van Aerschot A, Herdewijn P. Development of oligonucleotideconjugates with increased cellular uptake.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, Chaltin P, VanAerschot A, Herdewijn P. Oligopeptide-libraries for the sequence specificrecognition of nucleic acids.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, Lescrinier E, SchramlJ, Busson R, Esnouff R, Heres H, Hilbers C, Herdewijn P. Structure determinationof a HNA-RNA hybrid by NMR spectroscopy.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, Verbeure B,Herdewijn P. Synthesis of a ribozyme mimic.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, Zhang Z, VanAerschot A, Herdewijn P. Constrained guanidinium amino acids as ligands for HIV-1TAR-RNA.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, De Jonghe S, VanOvermeire I, De Keukeleire D, Herdewijn P. Synthesis of short-chaindihydroceramide analogues as potential substrates for dihydrioceramide desaturase.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, Van Calenbergh S,Vanheusden V, Link A, Herdewijn P. From adenosine A1 receptor agonist toantagonist by suitable sugar modification.

6-7 May, Forum des Sciences Pharmaceutique, Spa, Belgium, Van Overmeire I,Boldin S, De Keukeleire D, Futerman A, Herdewijn P. Study of new ceramideanalogues on the axonal growth of hippocampal neurons.

27-28 May, Les journées Franco-Belges de Pharmacochimie, Liège, Wouters J,Herdewijn P. Conformational analysis and interaction of anhydrohexitol nucleosideswith viral thymidine kinase.

2 September, Université Libre de Bruxelles, Faculté de Medicine, Institut derecherche interdisciplinaire en biologie humaine et nucleaire, Brussels, Belgium,Herdewijn P. Control of gene expression.

2000

5 April, 2nd Meeting on ^Crossing Borders in Mass Spectrometry], Antwerp,Belgium, Rozenski J, Verbeure B, Herdewijn P. Sequence analysis of modifiedoligonucleotides using electrospray with a quadrupole time of flight massspectrometer.

6-7 April, 9th Forum of Pharmaceutical Sciences, Blankenberge, Belgium, ChaltinP, Van Aerschot A, Hendrix C, Busson R, Herdewijn P. Selection and specificationof dsDNA interacting unnatural peptides.

6-7 April, 9th Forum of Pharmaceutical Sciences, Blankenberge, Belgium, VastmansK, Pochet S, Kerremans L, Hendrix C, Van Aerschot A., Herdewijn P. Elongationof a DNA primer with 1,5-anhydrohexitol nucleotides by means of DNApolymerase.

6-7 April, 9th Forum of Pharmaceutical Sciences, Blankenberge, Belgium, VerbeureB, Lacey C, Wang J, Herdewijn P. New RNA degrading constructs.

6-7 April, 9th Forum of Pharmaceutical Sciences, Blankenberge, Belgium, Zhang Z,Van Aerschot A, Herdewijn P. Effect of preactivation on the racemization ofunnatural amino acids.

10-14 July, 8th BOSS, Genth, Belgium, De Jonghe S, Van Calenbergh S, DeKeukeleire D, Herdewijn P. Synthesis of a novel type of ceramide analogues:homoceramides.

10-14 July, 8th BOSS, Genth, Belgium, Wang J, Herdewijn P. Enantioselectivesynthesis and conformational analysis of cyclohexene carbocyclic nucleosides.BSMS, UCB Pharma, Braine-lZAlleud, Rozenski J, Van Aerschot A, Herdewijn P.Incorporation of six-membered sugar rings in oligonucleotides and their effect onsequencing by mass spectrometry.

IV. Thesissen

Ceulemans G., Diverse stereomers of N-acylhydroxyprolinol as sugar substitute inoligonucleotides, 1997.

Samson I., Peptide libraries for de novo lead identification against TrypanosomaBrucei, 1997

Lescrinier T., Isolation of new peptide-based DNA-binding ligands usingcombinatorial chemistry, 1997

Lescrinier E., Structure determination of a HNA-RNA duplex by NMR spectroscopy,1999

V. Artikels in boeken of gedeelten van boeken

P. Herdewijn and E. De Clercq. Classical antiviral agents and design of new antiviralagents. In: Textbook of Medicinal Chemistry (Eds. Krogsgaard-Larsen P, JorgansenF.), 2nd Ed. Harwood Academic Publishers, 1996: 425-459.

Saison-Behmoaras E, Van Aerschot A, Duroux I, Hendrix C, Hélène C. HerdewijnP. Oligonucleotides : molecular versions for optimal use in vivo. In: Targeting ofDrugs 5: strategies for oligonucleotide and gene delivery in therapy (Eds.Gregoriadis and McCormack). Plenum Press, New York, 1996: 31-43.

Samson I, Kerremans L, Rozenski J, Van Aerschot A, Herdewijn P. De novo leadidentification against glycosomal phosphoglycerate kinase. In: Innovation andPerspectives in Solid Phase Synthesis and Combinatorial Libraries: Peptides,Proteins and Nucleic Acids (Eds. Epton R.). Mayflower Scientific, 1996: 523-524.

Van Aerschot A, Hendrix C, Verheggen I. Herdewijn P. Physicochemical propertiesof 1,5-anhydrohexitol nucleic acids. In: Innovation and Perspectives in Solid PhaseSynthesis and Combinatorial Libraries: Peptides, Proteins and Nucleic Acids (Eds.Epton R.), Mayflower Scientific, 1996: 69-72.

Herdewijn P. Nucleosides with a six membered carbohydrate moiety: structuralrequirement for antiviral activity, In: Anti-infectives: Recent Advances in Chemistryand Structure-Activity Relationships (Eds. Bentley PH, OZHanlon PJ), The RoyalSociety of Chemistry, 1997: 316-334.

Herdewijn P. Anhydrohexitols as conformationally constrained furanose mimics, thedesign of an RNA receptor. In: Carbohydrate Mimics: Concepts and Methods (Ed.Chapleur Y.), Wiley-VCH, Weinheim, 1998: 553-579.

Herdewijn P, Saison-Behmoaras E, Van Aerschot A, Duroux I, Leserman L, Eritja R,Pfleiderer W, Antisense oligonucleotides as anticancer agents. In: Cancer Research,Biomedical and Health Research, Vol. 24; I.O.S. Press, 1998: 182-189

De Bruyn A, Schraml J, Maras M, Contreras R, Herdewijn P. NMR techniques in thestudy of protein-linked carbohydrates. In: Carbohydrases from Trichoderma reeseiand other microorganisms, Royal Society of Chemistry Cambridge (Eds. ClaeyssensM, Nerinckx W, Piens K.), 1998: 315-322.

Maras M, De Bruyn A, Schraml J, Herdewijn P, Piens K, Claeyssens M, Uusitalo J,Penttila M, Fiers W, Contreras R. Engineering of the carbohydrate moiety of fungalproteins to a mammalian type. In: Carbohydrases from Trichoderma reesei andother microorganisms, Royal Society of Chemistry Cambridge (Eds. Claeyssens M,Nerinckx W, Piens K.), 1998: 323-326.

Lescrinier T, Hendrix C, Kerremans C, Rozenski J, Van Aerschot A, Herdewijn P.The use of peptide librans containing unnatural amino acids in the search for DNA-bonding ligands. In: Russian Journal of HIV (AIDS and related problems).

Saison-Behmoaras E, Herdewijn P, Van Berkel T, Laccetti P, Schneider M.Therapeutical potentialities of 3'-end modified antisense oligonucleotides targetedto codon 12 mutated Ha-ras. In: Cancer Research, Biomedical and Health Research,Vol. 24; I.O.S. Press, 1998: 27-29.

Verbeure B, Hendrix C, Van Aerschot A, Herdewijn P. Development of a ribozymemimic based on a di-imidazole catalytic moiety.

Zhang Z., Van Aerschot A, Hendrix C, Busson R, Herdewijn P. Basic amino acidswith amino or guanidinium substituents.

Wang J, Herdewijn P. Six-membered carbocyclic nucleosides with a purine basemoiety: synthesis, conformational analysis and antiviral activity.

Crain PF, Ruffner DE, Ho YH, Rozenski J, McCloskey JA. Problems and prospectsin the characterization of posttranscriptional modifications in large RNAs, MassSpectrometry Biol. Med., 2000; 531-551.

VI. Prijzen en onderscheidingen

2000

Prijs van het Fonds Dokter en Mevrouw SCHAMELHOUT _ KOETTLITZ, periode1998-1999 _ Van Aerschot A.

VII. Studieverblijven

14-19 September 1997.Lecturer ^New development in bioorganic chemistry], Association of the Swiss-French Universities, Champéry, Switzerland.

20-25 June 1999.Lecturer, International Ph.D. Summer School, Nucleic Acids Chemistry:Oligonucleotides and Analogues _ Synthesis, Structure and Properties,Copenhagen, Denmark.