1,7-DIDEAZA-2'-DEOXYADENOSINE - BUILDING-BLOCKS FOR SOLID-PHASE SYNTHESIS AND SECONDARY STRUCTURE OF BASE-MODIFIED OLIGODEOXYRIBONUCLEOTIDES
DC Element | Wert | Sprache |
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dc.contributor.author | SEELA, F | |
dc.contributor.author | WENZEL, T | |
dc.date.accessioned | 2021-12-23T16:01:13Z | - |
dc.date.available | 2021-12-23T16:01:13Z | - |
dc.date.issued | 1992 | |
dc.identifier.issn | 0018019X | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/4831 | - |
dc.description.abstract | The 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.iso | en | |
dc.publisher | NEW SWISS CHEMICAL SOC | |
dc.relation.ispartof | HELVETICA CHIMICA ACTA | |
dc.subject | 8-AZA-7-DEAZAADENINE | |
dc.subject | 9-FLUORENYLMETHOXYCARBONYL | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | DEOXYNUCLEOSIDES | |
dc.subject | DEPROTECTION | |
dc.subject | DNA | |
dc.subject | HAIRPIN FORMATION | |
dc.subject | OLIGONUCLEOTIDE SYNTHESIS | |
dc.subject | PROTECTION | |
dc.title | 1,7-DIDEAZA-2'-DEOXYADENOSINE - BUILDING-BLOCKS FOR SOLID-PHASE SYNTHESIS AND SECONDARY STRUCTURE OF BASE-MODIFIED OLIGODEOXYRIBONUCLEOTIDES | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/hlca.19920750414 | |
dc.identifier.isi | ISI:A1992JB45400013 | |
dc.description.volume | 75 | |
dc.description.issue | 4 | |
dc.description.startpage | 1111 | |
dc.description.endpage | 1122 | |
dc.publisher.place | VERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND | |
dcterms.isPartOf.abbreviation | Helv. Chim. Acta |
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geprüft am 29.04.2024