Synthesis of 9-halogenated 9-deazaguanine N-7-(2 `-deoxyribonucleosides)

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorShaikh, KI
dc.contributor.authorWiglenda, T
dc.contributor.authorLeonard, P
dc.date.accessioned2021-12-23T16:06:21Z-
dc.date.available2021-12-23T16:06:21Z-
dc.date.issued2004
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7369-
dc.description.abstractThe syntheses of N-7-glycosylated 9-deazaguanine 1a as well as of its 9-bromo and 9-iodo derivatives 1b,c are described. The regioselective 9-halogenation with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) was accomplished at the protected nucleobase 4a (2-{[(dimethylamino)methylidene]amino}-3,5-dihydro-3-[(pivaloyloxy )methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one). Nucleobase-anion glycosylation of 4a-c with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride (5) furnished the fully protected intermediates 6a-c (Scheme 2). They were deprotected with 0.01M NaOMe yielding the sugar-deprotected derivatives 8a-c (Scheme 3). At higher concentrations (0.1M NaOMe), also the pivaloyloxymethyl group was removed to give 7a-c, while conc. aq. NH3 solution furnished the nucleosides 1a-c. In D2O, the sugar conformation was always biased towards S (67-61%).
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDERIVATIVES
dc.subjectDNA
dc.subjectINHIBITORS
dc.subjectOLIGONUCLEOTIDE DUPLEXES
dc.subjectPURINE NUCLEOSIDE PHOSPHORYLASE
dc.subjectSTABILITY
dc.subjectSTRUCTURE-BASED DESIGN
dc.subjectSUBSTITUENTS
dc.subjectSUGAR CONFORMATION
dc.subjectTRIPLE-HELIX FORMATION
dc.titleSynthesis of 9-halogenated 9-deazaguanine N-7-(2 `-deoxyribonucleosides)
dc.typejournal article
dc.identifier.doi10.1002/hlca.200490224
dc.identifier.isiISI:000224935400003
dc.description.volume87
dc.description.issue10
dc.description.startpage2507
dc.description.endpage2516
dc.publisher.placePO BOX 10 11 61, D-69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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