A facile synthesis of D-glucose-type gem-diamine 1-N-iminosugars: A new family of glucosidase inhibitors

Authors
Shitara, E Nishimura, Y Kojima, F Takeuchi, T
Citation
E. Shitara et al., A facile synthesis of D-glucose-type gem-diamine 1-N-iminosugars: A new family of glucosidase inhibitors, BIO MED CH, 7(6), 1999, pp. 1241-1246
Citations number
35
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY
ISSN journal
09680896 → ACNP
Volume
7
Issue
6
Year of publication
1999
Pages
1241 - 1246
Database
ISI
SICI code
0968-0896(199906)7:6<1241:AFSODG>2.0.ZU;2-F
Abstract
gem-Diamine 1-N iminosugars of D-glucose-type, a new type of glycosidase in hibitors, have been synthesized from siastatin B, isolated from Streptomyce s culture. 2-Trifluoroacetamido-1-N-iminosugar, (2S,3R,4R,5R)-2-trifluoroac etamido-5-hydroxymethylpiperidine-3, 4-diol was proved to be a potent inhib itor for alpha-D- and P-D-glucosidases (IC50 1.9x10(-7) and 4.2x10(-7)M, re spectively). 2-Acetamido-1-N-iminosugar (2S,3R,4R, SR)-2-acetamido-5-hydrox ymethylpiperidine-3,4-diol also affected these enzymes (IC50 2.9x10(-6) and 5.4x10(-6) M, respectively). (C) 1999 Elsevier Science Ltd. All rights res erved.