Synthesis and antimicrobial activity of 2'-deoxypuromycin.
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).
Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University, Sendai, Japan.
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Koizumi
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Oritani
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Yamashita
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D011691:Puromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013055:Spectrophotometry, Infrared
D000900:Anti-Bacterial Agents; C069033:2'-deoxypuromycin; D011691:Puromycin