HOOGSTEEN-DUPLEX DNA - SYNTHESIS AND BASE-PAIRING OF OLIGONUCLEOTIDES CONTAINING 1-DEAZA-2'-DEOXYADENOSINE

DC FieldValueLanguage
dc.contributor.authorSEELA, F
dc.contributor.authorWENZEL, T
dc.date.accessioned2021-12-23T15:59:21Z-
dc.date.available2021-12-23T15:59:21Z-
dc.date.issued1994
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/3879-
dc.description.abstractOligodeoxyribonucleotides containing 1-deaza-2'-deoxyadenosine (= 7-amino-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3H-imidazo[4, 5-b]pyridine; 1b) form Hoogsteen duplexes. Watson-Crick base pairs cannot be built up due to the absence of N(1). For these studies, oligonucleotide building blocks - the phosphonate 3a and the phosphoramidite 3b - were prepared from 1b via 4a and 5, as well as the Fractosil-linked 6b, and used in solid-phase synthesis. The applicability of various N-protecting groups (see 4a-c) was also studied. The Hoogsteen duplex d[(c(1)A)(20].d(T?(20)) (11.13; T-m 15 degrees) is less stable than d(A(2)0).d(T-20) (12.13; T-m 60 degrees). The block oligomers d[(c(1)A)(10)-T-10] (14 and d[T-10-(c(1)A)(10] (15) containing purine and pyrimidine bases in the same strand are also able to form duplexes with each other. The chain polarity was found to be parallel.
dc.language.isoen
dc.publisherNEW SWISS CHEMICAL SOC
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subjectADENOSINE-DEAMINASE
dc.subjectBUILDING-BLOCKS
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectD(T)N.D(A)N.D(T)N
dc.subjectDEOXYNUCLEOSIDES
dc.subjectDEOXYRIBONUCLEOSIDES
dc.subjectOLIGODEOXYRIBONUCLEOTIDES
dc.subjectPHOSPHORAMIDITE
dc.subjectRIBONUCLEOSIDES
dc.subjectSOLID-PHASE SYNTHESIS
dc.subjectTRIPLE-HELIX FORMATION
dc.titleHOOGSTEEN-DUPLEX DNA - SYNTHESIS AND BASE-PAIRING OF OLIGONUCLEOTIDES CONTAINING 1-DEAZA-2'-DEOXYADENOSINE
dc.typejournal article
dc.identifier.doi10.1002/hlca.19940770604
dc.identifier.isiISI:A1994PH97600003
dc.description.volume77
dc.description.issue6
dc.description.startpage1485
dc.description.endpage1499
dc.publisher.placeVERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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