Synthesis of oligonucleotides containing pyrazolo[3,4-d]pyrimidines: The influence of 7-substituted 8-aza-7-deazaadenines on the duplex structure and stability

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorZulauf, M
dc.date.accessioned2021-12-23T15:59:50Z-
dc.date.available2021-12-23T15:59:50Z-
dc.date.issued1999
dc.identifier.issn0300922X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/4163-
dc.description.abstractThe phosphoramidites 2a-d derived from 7-bromo- (1b), 7-iodo- (1c), 7-(hex-1-ynyl)- (1d) and 7-(2-phenylethynyl)-(1e) 8-aza-7-deaza-2 `-deoxyadenosine were prepared. They were employed in the solid-phase synthesis of various oligonucleotides containing the 8-aza-7-deazaadenine system instead of that of adenine. Their T-m-values were measured and their thermodynamic data were determined. The replacement of adenine residues by 8-aza-7-deazaadenine 1a does not significantly influence the duplex stability, while the incorporation of 7-substituted derivatives 1b-e led to much more stable duplexes compared with their adenine-containing counterparts. From the CD spectra of the oligonucleotide duplexes it is evident that the overall structure of a parent DNA is retained when only very few modified bases are incorporated. Structural changes do occur when the number of modified residues is increased. This might be the result of the high-anti-conformation of the 7-substituted 8-aza-7-deaza-2'-deoxyadenosine residues.
dc.language.isoen
dc.publisherROYAL SOC CHEMISTRY
dc.relation.ispartofJOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
dc.subject2'-DEOXYRIBOFURANOSIDES
dc.subject7-DEAZAPURINE
dc.subject8-AZA-7-DEAZA-2'-DEOXYGUANOSINE
dc.subjectBASE
dc.subjectBUILDING-BLOCKS
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectDNA
dc.subjectGLYCOSIDIC CONFORMATION
dc.subjectHAIRPIN FORMATION
dc.subjectOLIGODEOXYRIBONUCLEOTIDES
dc.subjectSOLID-PHASE SYNTHESIS
dc.titleSynthesis of oligonucleotides containing pyrazolo[3,4-d]pyrimidines: The influence of 7-substituted 8-aza-7-deazaadenines on the duplex structure and stability
dc.typejournal article
dc.identifier.doi10.1039/a808769e
dc.identifier.isiISI:000079045500021
dc.description.issue4
dc.description.startpage479
dc.description.endpage488
dc.publisher.placeTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD,, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
dcterms.isPartOf.abbreviationJ. Chem. Soc.-Perkin Trans. 1
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