Synthesis and activity of 1-N-iminosugar inhibitors, siastatin B analogues for alpha-N-acetylgalactosaminidase and beta-N-acetylglucosaminidase

Bioorg Med Chem. 1996 Jan;4(1):91-6. doi: 10.1016/0968-0896(95)00166-2.

Abstract

N-Acetylgalactosamine-based 1-N-iminosugars, new types of glycosidase inhibitor have been synthesized by modeling on siastatin B, isolated from a Streptomyces culture. The analogues of siastatin B were proved to be potent inhibitors for alpha-N-acetylgalactosaminidase and/or beta-N-acetylglucosaminidase.

MeSH terms

  • Acetylglucosaminidase / antagonists & inhibitors*
  • Animals
  • Cattle
  • Chickens
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Epididymis / drug effects
  • Epididymis / enzymology
  • Hexosaminidases / antagonists & inhibitors*
  • Imino Pyranoses
  • Liver / drug effects
  • Liver / enzymology
  • Male
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry*
  • Piperidines / pharmacology
  • Structure-Activity Relationship
  • alpha-N-Acetylgalactosaminidase

Substances

  • 2-acetamido-5-hydroxymethylpiperidine-3,4-diol
  • Enzyme Inhibitors
  • Imino Pyranoses
  • Piperidines
  • siastatin
  • Hexosaminidases
  • alpha-N-Acetylgalactosaminidase
  • Acetylglucosaminidase