N-7-DNA - SYNTHESIS AND BASE PAIRING OF OLIGONUCLEOTIDES CONTAINING 7-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)ADENINE (N(7)A(D))
DC Element | Wert | Sprache |
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dc.contributor.author | SEELA, F | |
dc.contributor.author | WINTER, H | |
dc.date.accessioned | 2021-12-23T16:01:29Z | - |
dc.date.available | 2021-12-23T16:01:29Z | - |
dc.date.issued | 1994 | |
dc.identifier.issn | 0018019X | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/4985 | - |
dc.description.abstract | The synthesis of oligonucleotides containing 7-(2-deoxy-beta-D-erythro-pentofuranosyl)adenine (N(7)A(d); 1) is described. Compound 1 was obtained from the precursor 4-amino-1H-imidazole-5-carbonitrile 2-deoxyribonucleoside 6 and was found to be much more labile than A(d). The N-6-benzoyl protecting group (see 8) destabilized the N-glycosylic bond further and was difficult to remove by NH3-catalyzed hydrolysis. Therefore, a (dimethyl-amino)methylidene residue was introduced (--> 9). Amidine 9 was blocked at OH-C(5') with the dimethoxytrityl residue ((MeO)(2)Tr), and phosphonate 4 as well as phosphoramidite 5 were prepared under standard conditions. Phosphonate 4 was employed in solid-phase oligonucleotide synthesis. Homooligonucleotides as well as self-complementary oligonucleotides were prepared. The oligomer d[(N(7)A)(11)-A] (11) formed a duplex with d(T-12) (13). Antiparallel chain polarity and reverse Watson-Crick base pairing was deduced from duplex formation of the self-complementary d[(N(7)A)(8)-T-8] (14). | |
dc.language.iso | en | |
dc.publisher | NEW SWISS CHEMICAL SOC | |
dc.relation.ispartof | HELVETICA CHIMICA ACTA | |
dc.subject | BUILDING-BLOCKS | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | DOUBLE HELIX | |
dc.subject | GLYCOSYLATION | |
dc.subject | OLIGODEOXYRIBONUCLEOTIDES | |
dc.subject | PARALLEL | |
dc.subject | RELATIVE STABILITY | |
dc.subject | STRANDED DUPLEX DNA | |
dc.title | N-7-DNA - SYNTHESIS AND BASE PAIRING OF OLIGONUCLEOTIDES CONTAINING 7-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)ADENINE (N(7)A(D)) | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/hlca.19940770302 | |
dc.identifier.isi | ISI:A1994NM08200001 | |
dc.description.volume | 77 | |
dc.description.issue | 3 | |
dc.description.startpage | 597 | |
dc.description.endpage | 607 | |
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 14.05.2024