Totally synthetic analogues of siastatin B. II. Optically active piperidine derivatives having trifluoroacetamide and hydroxyacetamide groups at C-2.
Siastatin B analogues, optically active 2-(trifluoroacetamide)- 3,4,5-trihydroxypiperidines having nitromethyl, aminomethyl and carboxyl branched groups at C-5, and (+)-(2R,3R,4R,5R)-5-(aminomethyl)-3,4,5-trihydroxy-2- (hydroxyacetamido)piperidine have been obtained total synthetically from D-ribono-1,4-lactone. Some analogues have inhibitory activity against some glycosidases, and (+)-(2R,3R,4R,5R)-2-(trifluoroacetamido)-3,4,5-trihydroxypiperi dine-5-carboxylic acid showed a marked inhibitory activity against beta-glucuronidase.
Nishimura
Y
Y
Institute of Microbial Chemistry, Tokyo, Japan.
Kudo
T
T
Kondo
S
S
Takeuchi
T
T
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D010880:Piperidines
D000900:Anti-Bacterial Agents; D010880:Piperidines; C011353:siastatin; D006026:Glycoside Hydrolases; D009439:Neuraminidase