N-7-DNA: Base-pairing properties of N-7-(2 `-deoxy-beta-D-erythro-pentofuranosyl)-substituted adenine, hypoxanthine, and guanine in duplexes with parallel chain orientation

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorLeonard, P
dc.date.accessioned2021-12-23T15:59:50Z-
dc.date.available2021-12-23T15:59:50Z-
dc.date.issued1998
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/4167-
dc.description.abstractOligonucleotides containing N-7-(2'-deoxy-beta-D-erythro-pentofuranosyl)adenine (1),-hypoxanthine (2), and -guanine (3) were synthesized on solid-phase using phosphonate and phosphoramidite chemistry. As part of the synthesis of compound 2. the nucleobase-anion glycosylation of various 6-alkoxypurines with 2-droxy-3,5-di-O-(4-toluoyl)-alpha-D-erythro-pentofuranosyl chloride (5) was investigated. The duplex stability of oligonucleotides containing N-7-glycosylated purines opposite to regular pyrimidines was determined, and thermodynamic data were calculated from melting profiles. Oligodeoxyribonucleotide duplexes containing N-7-glycosylated adenine T-d or N-7-glycosylated guanine Cd base pairs are more stable in the case of parallel strand orientation than in the case of antiparallel chains.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subjectBUILDING-BLOCKS
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDEOXYINOSINE
dc.subjectGLYCOSYLATION
dc.subjectN-7-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)GUANINE N(7)G(D)
dc.subjectOLIGODEOXYRIBONUCLEOTIDES
dc.subjectOLIGONUCLEOTIDES
dc.subjectRECOGNITION
dc.subjectSOLID-PHASE SYNTHESIS
dc.subjectSTABILITY
dc.subjectTRIPLE-HELIX FORMATION
dc.titleN-7-DNA: Base-pairing properties of N-7-(2 `-deoxy-beta-D-erythro-pentofuranosyl)-substituted adenine, hypoxanthine, and guanine in duplexes with parallel chain orientation
dc.typejournal article
dc.identifier.isiISI:000077817900006
dc.description.volume81
dc.description.issue12
dc.description.startpage2244
dc.description.endpage2263
dc.publisher.placeBOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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