Pyrazolo[3,4-d][1,2,3]triazine DNA: Synthesis and base pairing of 7-deaza-2,8-diaza-2 `-deoxyadenosine

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorLindner, M
dc.contributor.authorGlacon, V
dc.contributor.authorLin, WQ
dc.date.accessioned2021-12-23T16:05:40Z-
dc.date.available2021-12-23T16:05:40Z-
dc.date.issued2004
dc.identifier.issn00223263
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7137-
dc.description.abstract7-Deaza-2,8-diaza-2'-deoxyadenosine (4) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (1) via the 1,N-6-etheno derivative 5. Ring opening with sodium hydroxide followed by ring closure in the presence of sodium nitrite formed the tricyclic intermediate 5 from which the transiently introduced ``etheno'' moiety was removed with NBS. Compound 4 was converted to the phosphoramidite 11, which was employed in solid-phase oligonucleotide synthesis. Base pairing studies on 4, incorporated in a 12-mer duplex, showed that this adenine nucleoside analogue forms a strong base pair with dG but not with dT. This novel base pair is as stable as that of the canonical dA-dT pair. As a result of the absence of nitrogen-7 compound 4 is expected to form a face to face base pair with dG.
dc.language.isoen
dc.publisherAMER CHEMICAL SOC
dc.relation.ispartofJOURNAL OF ORGANIC CHEMISTRY
dc.subject2',3'-DIDEOXYRIBONUCLEOSIDES
dc.subject2'-DEOXYRIBOFURANOSIDES
dc.subjectANALOGS
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectDERIVATIVES
dc.subjectGLYCOSYLATION
dc.subjectIMIDAZOLE NUCLEOSIDES
dc.subjectNUCLEOBASE-ANION
dc.subjectOLIGONUCLEOTIDES
dc.subjectPURINE
dc.subjectSTABILITY
dc.titlePyrazolo[3,4-d][1,2,3]triazine DNA: Synthesis and base pairing of 7-deaza-2,8-diaza-2 `-deoxyadenosine
dc.typejournal article
dc.identifier.doi10.1021/jo040150i
dc.identifier.isiISI:000222449200017
dc.description.volume69
dc.description.issue14
dc.description.startpage4695
dc.description.endpage4700
dc.publisher.place1155 16TH ST, NW, WASHINGTON, DC 20036 USA
dcterms.isPartOf.abbreviationJ. Org. Chem.
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