1,7-DIDEAZA-2'-DEOXYADENOSINE - BUILDING-BLOCKS FOR SOLID-PHASE SYNTHESIS AND SECONDARY STRUCTURE OF BASE-MODIFIED OLIGODEOXYRIBONUCLEOTIDES

DC FieldValueLanguage
dc.contributor.authorSEELA, F
dc.contributor.authorWENZEL, T
dc.date.accessioned2021-12-23T16:01:13Z-
dc.date.available2021-12-23T16:01:13Z-
dc.date.issued1992
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/4831-
dc.description.abstractThe 1,7-dideaza-2'-deoxyadenosine (c1c7A(d); 1) was converted into building blocks 3a,b for solid-phase oligodeoxyribonucleotide synthesis. Testing various N-protecting groups - benzoyl, phenoxyacetyl, [(fluoren-9-yl)methoxy]carbonyl, and (dimethylamino)methylidene - only the latter two were found to be suitable (1 --> 4b, d). Ensuing 4,4'-dimethoxytritylation of 4d and phosphitylation afforded the 3'-phosphonate 3a or the 3'-[(2-cyanoethyl)diisopropylphosphoramidite] 3b. Self-complementary oligonucleotides with alternating dA or c1c'A(d) and dT residues (7 and 8) as well as palindromic oligomers such as d(C-G-C-G-c1c7A-c1C7A-T-T-C-G-C-G) (10) and d(G-T-A-G-c1c7A-c1c7A-T-T-C-T-A-C) (12) were synthesized. Duplex stability was decreased because 1 cannot form Watson-Crick or Hoogsteen base pairs if incorporated into oligonucleotides. On the other hand, the structural modifications in 10 and 12 forced these palindromic oligomers to form hairpin structures.
dc.language.isoen
dc.publisherNEW SWISS CHEMICAL SOC
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subject8-AZA-7-DEAZAADENINE
dc.subject9-FLUORENYLMETHOXYCARBONYL
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDEOXYNUCLEOSIDES
dc.subjectDEPROTECTION
dc.subjectDNA
dc.subjectHAIRPIN FORMATION
dc.subjectOLIGONUCLEOTIDE SYNTHESIS
dc.subjectPROTECTION
dc.title1,7-DIDEAZA-2'-DEOXYADENOSINE - BUILDING-BLOCKS FOR SOLID-PHASE SYNTHESIS AND SECONDARY STRUCTURE OF BASE-MODIFIED OLIGODEOXYRIBONUCLEOTIDES
dc.typejournal article
dc.identifier.doi10.1002/hlca.19920750414
dc.identifier.isiISI:A1992JB45400013
dc.description.volume75
dc.description.issue4
dc.description.startpage1111
dc.description.endpage1122
dc.publisher.placeVERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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