1-(2'-DEOXY-BETA-D-XYLOFURANOSYL)THYMINE BUILDING-BLOCKS FOR SOLID-PHASE SYNTHESIS AND PROPERTIES OF OLIGO(2'-DEOXYXYLONUCLEOTIDES)

DC FieldValueLanguage
dc.contributor.authorROSEMEYER, H
dc.contributor.authorSEELA, F
dc.date.accessioned2021-12-23T16:03:25Z-
dc.date.available2021-12-23T16:03:25Z-
dc.date.issued1991
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/5978-
dc.description.abstract1-(2'-Deoxy-beta-D-threo-pentofuranosyl)thymine (= 1-(2'-deoxy-beta-D-xylofuranosyl)thymine; xT(d); 2) was converted into its phosphonate 3b as well as its 2-cyanoethyl phosphoramidite 3c. Both compounds were used for solid-phase synthesis of d[(xT)12-T] (5), representing the first DNA fragment build up from 3'-5'-linked 2'-deoxy-beta-D-xylonucleosides. Moreover, xT(d) was introduced into the innermost part of the self-complementary dodecamer d(G-T-A-G-A-A-xT-xT-C-T-A-C)2 (9). The CD spectrum of d[(xT)12-T] (5) exhibits reversed Cotton effects compared to d(T12) (6; see Fig. 1), implying a left-handed single strand. With d(A12) (7) it could be hybridized to form a propably left-handed double strand d(A12).d[(xT)12-T] (7.5) which was confirmed by melting experiments in combination with temperature-dependent CD spectroscopy. While 5 was hydrolyzed by snake-venom phosphodiesterase, it was resistant towards calf-spleen phosphodiesterase. The modified, self-complementary duplex 9 was hydrolyzed completely by snake-venom phosphodiesterase, at a twelvefold slower rate compared to unmodified 8; calf-spleen phosphodiesterase hydrolyzed 9 only partially.
dc.language.isoen
dc.publisherNEW SWISS CHEMICAL SOC
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectCONFORMATIONAL-ANALYSIS
dc.subjectDEOXYADENOSINE
dc.subjectNUCLEOSIDES
dc.subjectNUCLEOTIDES
dc.subjectSUGAR RING
dc.title1-(2'-DEOXY-BETA-D-XYLOFURANOSYL)THYMINE BUILDING-BLOCKS FOR SOLID-PHASE SYNTHESIS AND PROPERTIES OF OLIGO(2'-DEOXYXYLONUCLEOTIDES)
dc.typejournal article
dc.identifier.doi10.1002/hlca.19910740408
dc.identifier.isiISI:A1991FU74800007
dc.description.volume74
dc.description.issue4
dc.description.startpage748
dc.description.endpage760
dc.publisher.placeVERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND
dcterms.isPartOf.abbreviationHelv. Chim. Acta
crisitem.author.deptInstitut für Chemie neuer Materialien-
crisitem.author.deptidinstitute11-
crisitem.author.parentorgFB 05 - Biologie/Chemie-
crisitem.author.grandparentorgUniversität Osnabrück-
crisitem.author.netidRoHe783-
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