5-aza-7-deaza-2 `-deoxyguanosine: Oligonucleotide duplexes with novel base pairs, parallel chain orientation and protonation sites in the core of a double helix

Autor(en): Seela, F
Melenewski, A
Stichwörter: 5-aza-7-deaza-2 `-deoxyguanosine; 7-DEAZAPURINE; 8-AZA-7-DEAZAADENINE; BUILDING-BLOCKS; Chemistry; Chemistry, Organic; DNA-SYNTHESIS; GLYCOSYLATION; OLIGODEOXYRIBONUCLEOTIDES; oligonucleotides; parallel DNA; PROTECTION; protonated base pairs; RECOGNITION; SOLID-PHASE SYNTHESIS; STABILITY; T-m values
Erscheinungsdatum: 1999
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volumen: 1999
Ausgabe: 2
Startseite: 485
Seitenende: 496
Zusammenfassung: 
Oligonucleotides containing 5-aza-7-deaza-2'-deoxyguanosine (1) were synthesized. Solid-phase synthesis was performed with the phosphonate 15 or the phosphoramidite 5. The amino-unprotected phosphonate 4 was also employed. Hybridization studies of oligonucleotides containing 1 resulted in new base pairs leading to duplexes with parallel tps) or antiparallel taps) chain orientation. Among those with parallel chains a stable ``purine-purine'' base pair was observed between 5-aza-7-deazaguanine and guanine or 7-deazaguanine. Antiparallel stranded duplexes are formed when 5-aza-7-deazaguanine pairs with cytosine. This base pair has only two hydrogen bonds under neutral conditions but is stabilized by a third one in acidic medium. A new base pair is also detected between the base of 1 and isoguanine (neutral medium).
ISSN: 1434193X
DOI: 10.1002/(SICI)1099-0690(199902)1999:2<485::AID-EJOC485>3.0.CO;2-J

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