Synthesis of a carbohydrate-derived hydroxamic acid inhibitor of the bacterial enzyme (LpxC) involved in lipid A biosynthesis

Org Lett. 2003 Feb 20;5(4):539-41. doi: 10.1021/ol027458l.


[reaction: see text] The enzyme LpxC (UDP-3-O-[(R)-3-hydroxymyristoyl]-GlcNAc deacetylase) catalyzes the second step of lipid A biosynthesis and is essential for bacterial growth. A GlcNAc-derived hydroxamic acid inhibitor 8 of this enzyme was synthesized using two different routes. Compound 8 exhibits activity toward LpxC enzymes from a wider spectrum of bacterial species than any of the previously reported hydroxamic acid inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amidohydrolases / antagonists & inhibitors*
  • Carbohydrates / chemistry
  • Enzyme Inhibitors / chemical synthesis
  • Escherichia coli Proteins / antagonists & inhibitors
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / pharmacology
  • Lipid A / antagonists & inhibitors
  • Lipid A / biosynthesis


  • Carbohydrates
  • Enzyme Inhibitors
  • Escherichia coli Proteins
  • Hydroxamic Acids
  • Lipid A
  • Amidohydrolases
  • UDP-3-O-acyl-N-acetylglucosamine deacetylase