Novel S-ribosylhomocysteine analogues as potential inhibitors of LuxS enzyme

Nucleosides Nucleotides Nucleic Acids. 2007;26(8-9):1051-5. doi: 10.1080/15257770701513190.

Abstract

Selective cross-coupling of the protected 6-fluoro-6-iodo-alpha-D-ribo-hex-5-enofuranose with 2 equivalents of 4-ethoxy-4-oxobutylzinc bromide in the presence of Pd[P(Ph)(3)](4) followed by deprotections gave methyl 5,6,7,8,9-pentadeoxy-6-fluoro-alpha/beta-D-ribo-dec-5(Z)-enofuranuronate; a S-ribosylhomocysteine analogue with the sulfur and carbon-5 atoms replaced by the fluoro(vinyl) unit.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Bacterial Proteins / antagonists & inhibitors*
  • Carbon-Sulfur Lyases / antagonists & inhibitors*
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Homocysteine / analogs & derivatives*
  • Homocysteine / chemical synthesis
  • Homocysteine / chemistry
  • Homocysteine / pharmacology

Substances

  • Bacterial Proteins
  • Enzyme Inhibitors
  • S-ribosyl-L-homocysteine
  • Homocysteine
  • Carbon-Sulfur Lyases
  • LuxS protein, Bacteria