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Synthesis and antimicrobial activity of 2'-deoxypuromycin
F Koizumi1, T Oritani, K Yamashita
1Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University, Sendai, Japan.
Agricultural and Biological Chemistry
|December 1, 1990
Abstract:
2'-Deoxypuromycin (2) was synthesized to learn the effect of the 2'-hydroxyl group on the biological activity. Acylated xylose 3 was condensed with silylated 6-chloropurine to give beta-D-xylofuranosyl-6-chloropurine derivative 4, whose 6-dimethylamination, 2'-deoxygenation and deprotection afforded 2'-deoxy-beta-D-xylofuranosyl purine analog 7. The latter was converted to 2'-deoxypuromycin (2) in 8 steps. 2'-Deoxy analog 2 showed only weak antimicrobial activity compared with that of puromycin (1).