Synthesis of delta4-beta-D-glucopyranosiduronic acids as mimetics of 2,3-unsaturated sialic acids for sialidase inhibition

Bioorg Med Chem Lett. 1999 Jul 19;9(14):2065-8. doi: 10.1016/s0960-894x(99)00331-5.

Abstract

Mimetics of Neu5Ac2en and KDN2en, based on delta4-beta-delta-glucopyranosiduronic acids, have been synthesised. The Neu5Ac2en mimetic 5 showed inhibition of both bacterial and viral sialidases, with inhibition of the viral sialidase being comparable to that of Neu5Ac2en itself.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Drug Evaluation, Preclinical
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Glucuronates / chemical synthesis*
  • Glucuronates / pharmacology*
  • Influenza A virus / enzymology
  • Molecular Mimicry
  • N-Acetylneuraminic Acid / analogs & derivatives
  • N-Acetylneuraminic Acid / chemistry
  • Neuraminidase / antagonists & inhibitors*
  • Ostreidae / enzymology
  • Salmonella typhimurium / enzymology
  • Sialic Acids / chemistry
  • Sialic Acids / metabolism
  • Structure-Activity Relationship
  • Vibrio cholerae / enzymology

Substances

  • 2-deoxy-2,3-didehydro-D-glycero-D-galacto-2-nonulopyranosonic acid
  • Enzyme Inhibitors
  • Glucuronates
  • Sialic Acids
  • 2-deoxy-2,3-dehydro-N-acetylneuraminic acid
  • Neuraminidase
  • N-Acetylneuraminic Acid