Rapid preparation of mycobacterium N-glycolyl Lipid I and Lipid II derivatives: a biocatalytic approach

Chemistry. 2013 Jan 14;19(3):834-8. doi: 10.1002/chem.201203251. Epub 2012 Dec 11.

Abstract

Breaking down barriers: A rapid, inexpensive preparation of the structurally complex mycobacterial N-glycolyl Lipid I, Lipid II, and their analogues from a range of different synthetic N-glycolyl and N-glycinyl Park's nucleotides is described (see scheme). The biotransformations were catalyzed by a readily available biocatalyst obtained from a bacterial cell-free membrane fraction. The unnatural N-glycinyl Lipid II was found to be a substrate of Mycobacterium tuberculosis (Mtb) transglycosylase, PonA, and N-glycolyl Lipid I was a weak inhibitor against PonA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Outer Membrane Proteins / metabolism*
  • Bacterial Proteins / metabolism*
  • Biocatalysis
  • Glycolipids / biosynthesis*
  • Glycolipids / chemistry
  • Glycolipids / metabolism
  • Molecular Structure
  • Mycobacterium tuberculosis / chemistry*
  • Mycobacterium tuberculosis / enzymology
  • Mycobacterium tuberculosis / metabolism
  • N-Acetylglucosaminyltransferases / metabolism*
  • Transferases (Other Substituted Phosphate Groups)
  • Transferases / metabolism*

Substances

  • Bacterial Outer Membrane Proteins
  • Bacterial Proteins
  • Glycolipids
  • Transferases
  • N-Acetylglucosaminyltransferases
  • UDP-N-acetylglucosamine-N-acetylmuramyl-(pentapeptide)pyrophosphoryl-undecaprenol N-acetylglucosamine transferase
  • Transferases (Other Substituted Phosphate Groups)
  • mraY protein, Bacteria