7-deazaadenine-DNA: Bulky 7-iodo substituents or hydrophobic 7-hexynyl chains are well accommodated in the major groove of oligonucleotide duplexes

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorZulauf, M
dc.date.accessioned2021-12-23T16:01:26Z-
dc.date.available2021-12-23T16:01:26Z-
dc.date.issued1998
dc.identifier.issn09476539
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/4957-
dc.description.abstractOligonucleotides containing 7-deaza-7-(hex-1-ynyl)-2'-deoxyadenosine (1) and 7-deaza-7-iodo-2'-deoxyadenosine (2) are described. The corresponding phosphoramidites (3 a,b) were synthesized and employed in solid-phase oligonucleotide synthesis. The modified 7-deazaadenine residues show selective base-pairing with dT. According to the T-m values and the thermodynamic data of duplex formation, the 7-iodo and the 7-(hex-1-ynyl) residues of a 7-deazaadenine moiety increase the duplex stability with retention of the particular DNA structure. This is different from 8-substituted adenine, which destabilizes the nucleic acid duplex significantly. The nucleoside 1 fluoresces strongly.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofCHEMISTRY-A EUROPEAN JOURNAL
dc.subject2'-DEOXYTUBERCIDIN
dc.subject7-DEAZA-2'-DEOXYADENOSINE
dc.subject7-IODO-2'-DEOXYTUBERCIDIN
dc.subjectB-DNA
dc.subjectBASE
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDNA structures
dc.subjectduplex stability
dc.subjectGLYCOSIDIC CONFORMATION
dc.subjectHAIRPIN FORMATION
dc.subjectnucleosides
dc.subjectOLIGODEOXYNUCLEOTIDES
dc.subjectoligonucleosides
dc.subjectPROPYNE ANALOGS
dc.subjectSUGAR CONFORMATION
dc.title7-deazaadenine-DNA: Bulky 7-iodo substituents or hydrophobic 7-hexynyl chains are well accommodated in the major groove of oligonucleotide duplexes
dc.typejournal article
dc.identifier.doi10.1002/(SICI)1521-3765(19980904)4:9<1781::AID-CHEM1781>3.0.CO;2-K
dc.identifier.isiISI:000075861500024
dc.description.volume4
dc.description.issue9
dc.description.startpage1781
dc.description.endpage1790
dc.publisher.placeMUHLENSTRASSE 33-34, D-13187 BERLIN, GERMANY
dcterms.isPartOf.abbreviationChem.-Eur. J.
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