The high-anti conformation of 7-halogenated 8-aza-7-deaza-2 `-deoxyguanosines: A study of the influence of modified bases on the sugar structure of nucleosides

Autor(en): Seela, F
Becher, G
Rosemeyer, H 
Reuter, H 
Kastner, G
Mikhailopulo, IA
Stichwörter: 500-MHZ H-1-NMR SPECTROSCOPY; ANALOGS; C-NUCLEOSIDES; Chemistry; Chemistry, Multidisciplinary; CRYSTAL-STRUCTURE; DNA; DUPLEX STABILITY; GAUCHE; PENTOFURANOSE MOIETY; PSEUDOROTATIONAL EQUILIBRIUM; SOLID-STATE
Erscheinungsdatum: 1999
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 82
Ausgabe: 1
Startseite: 105
Seitenende: 124
Zusammenfassung: 
The conformation of the 7-bromo- and 7-iodo-substituted 8-aza-7-deazapurine nucleosides 1 and 2 in the solid state and in aqueous solution was studied by single-crystal X-ray analyses and by H-1-NMR spectroscopy. In the solid state, both compounds display a high-anti conformation around the glycosylic bond, and their 2'-deoxy-beta-D-ribofuranose moieties adopt an N-type sugar puckering. The orientation of the exocyclic C(4')-C(5') bond was found to be crp in both cases. In D2O solution, both compounds display i) an 8-10% higher N-conformer population than 2'-deoxyguanosine and ii) a preference of the -sc conformation about the C(4')-C(5') bond. A comparative study on the influence of modified bases on the sugar structure of nucleosides is made.
ISSN: 0018019X
DOI: 10.1002/(SICI)1522-2675(19990113)82:1<105::AID-HLCA105>3.0.CO;2-3

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