Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-β-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4one (2'-deoxy-9- deazaguanosine)

Eric S. Gibson, Krystyna Lesiak, Kyoichi A. Watanabe, Lorraine J. Gudas, Krzysztof W. Pankiewicz

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14 Scopus citations

Abstract

A synthesis of the C-nucleoside, 2-amino-7-(2-deoxy-β-D- erythropentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (9-deaza-2'- deoxyguanosine) was achieved starting from 2-amino-6-methyl-3H-pyrimidin-4- one (5) and methyl 2-deoxy-3,5-di-O-(p-nitrobenzoyl)-D-erythro-pento- furanoside (11). The anomeric configuration of the C-nucleoside was established by 1H NMR, NOEDS and ROESY. This C-nucleoside did not inhibit the growth of T-cell lymphoma cells.

Original languageEnglish (US)
Pages (from-to)363-376
Number of pages14
JournalNucleosides and Nucleotides
Volume18
Issue number3
DOIs
StatePublished - Jan 1 1999

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