A facile synthesis of d-glucose-type gem-diamine 1-N-iminosugars: a new family of glucosidase inhibitors Original Research Article

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 α-d- and β-d-glucosidases (IC50 1.9×10−7 and 4.2×10−7 M, respectively). 2-Acetamido-1-N-iminosugar, (2S,3R,4R,5R)-2-acetamido-5-hydroxymethylpiperidine-3,4-diol also affected these enzymes (IC50 2.9×10−6 and 5.4×10−6 M, respectively).