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

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorBecher, G
dc.contributor.authorRosemeyer, H
dc.contributor.authorReuter, H
dc.contributor.authorKastner, G
dc.contributor.authorMikhailopulo, IA
dc.date.accessioned2021-12-23T16:13:07Z-
dc.date.available2021-12-23T16:13:07Z-
dc.date.issued1999
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/10415-
dc.description.abstractThe 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.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subject500-MHZ H-1-NMR SPECTROSCOPY
dc.subjectANALOGS
dc.subjectC-NUCLEOSIDES
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectCRYSTAL-STRUCTURE
dc.subjectDNA
dc.subjectDUPLEX STABILITY
dc.subjectGAUCHE
dc.subjectPENTOFURANOSE MOIETY
dc.subjectPSEUDOROTATIONAL EQUILIBRIUM
dc.subjectSOLID-STATE
dc.titleThe 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
dc.typereview
dc.identifier.doi10.1002/(SICI)1522-2675(19990113)82:1<105::AID-HLCA105>3.0.CO;2-3
dc.identifier.isiISI:000078263800011
dc.description.volume82
dc.description.issue1
dc.description.startpage105
dc.description.endpage124
dc.contributor.researcheridH-9847-2014
dc.identifier.eissn15222675
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationHelv. Chim. Acta
crisitem.author.deptInstitut für Chemie neuer Materialien-
crisitem.author.deptInstitut für Chemie neuer Materialien-
crisitem.author.deptidinstitute11-
crisitem.author.deptidinstitute11-
crisitem.author.parentorgFB 05 - Biologie/Chemie-
crisitem.author.parentorgFB 05 - Biologie/Chemie-
crisitem.author.grandparentorgUniversität Osnabrück-
crisitem.author.grandparentorgUniversität Osnabrück-
crisitem.author.netidRoHe783-
crisitem.author.netidReHa636-
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