Synthesis of Cytidine, Uridine, and Adenosine 5′-(2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl diphosphates)(Neosamine C-CDP, -UDP, and -ADP)

Three potential biosynthetic intermediates for aminocyclitol antibiotics, neosamine C-CDP, -UDP, and -ADP, have been synthesized from D-glucosamine by chemical means. 2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl phosphate, derived from the corresponding glycosyl bromide, was condensed with three nucle...

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Published inBulletin of the Chemical Society of Japan Vol. 55; no. 12; pp. 3840 - 3846
Main Authors Tadano, Kin-ichi, Tsuchiya, Tohru, Suami, Tetsuo, Rinehart, Kenneth L
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.12.1982
Chemical Society of Japan
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Summary:Three potential biosynthetic intermediates for aminocyclitol antibiotics, neosamine C-CDP, -UDP, and -ADP, have been synthesized from D-glucosamine by chemical means. 2,6-Diamino-2,6-dideoxy-α-D-glucopyranosyl phosphate, derived from the corresponding glycosyl bromide, was condensed with three nucleosides (CMP, UMP and AMP) by a known procedure. The configurations of the neosamine C nucleoside diphosphates have been confirmed by 13C NMR spectra.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.55.3840