A facile synthesis of D-glucose-type gem-diamine 1-N-iminosugars: a new family of glucosidase inhibitors.
gem-Diamine 1-N iminosugars of D-glucose-type, a new type of glycosidase inhibitors, have been synthesized from siastatin B, isolated from Streptomyces culture. 2-Trifluoroacetamido-1-N-iminosugar, (2S,3R,4R,5R)-2-trifluoroacetamido-5-hydroxymethylpiperidine -3,4-diol was proved to be a potent inhibitor for alpha-D- and beta-D-glucosidases (IC50 1.9x10(-7) and 4.2x10(-7) M, respectively). 2-Acetamido-1-N-iminosugar, (2S,3R,4R,5R)-2-acetamido-5-hydroxymethylpiperidine-3,4-diol also affected these enzymes (IC50 2.9x10(-6) and 5.4x10(-6) M, respectively).
Shitara
E
E
Institute of Microbial Chemistry, Tokyo, Japan.
Nishimura
Y
Y
Kojima
F
F
Takeuchi
T
T
D001234:Aspergillus niger / Q000201:enzymology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D005959:Glucosidases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010880:Piperidines / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry
C120956:5-hydroxymethyl-2-trifluoroacetamidopiperidine-3,4-diol; D004791:Enzyme Inhibitors; D010880:Piperidines; C011353:siastatin; D005959:Glucosidases