The N-8-(2 `-deoxyribofuranoside) of 8-aza-7-deazaadenine : a universal nucleoside forming specific hydrogen bonds with the four canonical DNA constituents

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorDebelak, H
dc.date.accessioned2021-12-23T16:03:20Z-
dc.date.available2021-12-23T16:03:20Z-
dc.date.issued2000
dc.identifier.issn03051048
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/5930-
dc.description.abstractThe 8-aza-7-deazaadenine (pyrazolo[3,4-d]pyrimidin-4-amine) N-8-(2'-deoxyribonucleoside) (2) which has an unusual glycosylation position was introduced as a universal nucleoside in oligonucleotide duplexes. These oligonucleotides were prepared by solid-phase synthesis employing phosphoramidite chemistry. Oligonucleotides incorporating the universal nucleoside 2 are capable of forming base pairs with the four normal DNA nucleosides without significant structural discrimination. The thermal stabilities of those duplexes are very similar and are only moderately reduced compared to those with regular Watson-Crick base pairs, The universal nucleoside 2 belongs to a new class of compounds that form bidentate base pairs with all four natural DMA constituents through hydrogen bonding. The base pair motifs follow the Watson-Crick or the Hoogsteen mode. Also an uncommon motif is suggested for the base pair of 2 and dG. All of the new base pairs have a different shape compared to those of the natural DNA but fit well into the DNA duplex as the distance of the anomeric carbons approximates those of the common DNA base pairs.
dc.language.isoen
dc.publisherOXFORD UNIV PRESS
dc.relation.ispartofNUCLEIC ACIDS RESEARCH
dc.subject5-NITROINDOLE
dc.subjectANALOGS
dc.subjectBASES
dc.subjectBiochemistry & Molecular Biology
dc.subjectBUILDING-BLOCKS
dc.subjectDEOXYINOSINE
dc.subjectDUPLEX STABILITY
dc.subjectNUCLEOSIDE
dc.subjectOLIGODEOXYRIBONUCLEOTIDES
dc.subjectOLIGONUCLEOTIDES
dc.subjectPRIMERS
dc.titleThe N-8-(2 `-deoxyribofuranoside) of 8-aza-7-deazaadenine : a universal nucleoside forming specific hydrogen bonds with the four canonical DNA constituents
dc.typejournal article
dc.identifier.doi10.1093/nar/28.17.3224
dc.identifier.isiISI:000089078900005
dc.description.volume28
dc.description.issue17
dc.description.startpage3224
dc.description.endpage3232
dc.publisher.placeGREAT CLARENDON ST, OXFORD OX2 6DP, ENGLAND
dcterms.isPartOf.abbreviationNucleic Acids Res.
dcterms.oaStatusGreen Published
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