Synthesis and evaluation of a new fluorescent transglycosylase substrate: lipid II-based molecule possessing a dansyl-C20 polyprenyl moiety

Org Lett. 2010 Apr 2;12(7):1608-11. doi: 10.1021/ol100338v.

Abstract

The preparation of a novel fluorescent lipid II-based substrate for transglycosylases (TGases) is described. This substrate has characteristic structural features including a shorter lipid chain, a fluorophore tag at the end of the lipid chain rather than on the peptide chain, and no labeling with a radioactive atom. This fluorescent substrate is readily utilized in TGase activity assays to characterize TGases and also to evaluate the activities of TGase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bambermycins / pharmacology
  • Enzyme Inhibitors / pharmacology
  • Fluorescence*
  • Glycosyltransferases / antagonists & inhibitors
  • Glycosyltransferases / metabolism*
  • Molecular Structure
  • Polyisoprenyl Phosphates / chemical synthesis*
  • Polyisoprenyl Phosphates / chemistry
  • Polyisoprenyl Phosphates / metabolism*
  • Structure-Activity Relationship
  • Substrate Specificity
  • Uridine Diphosphate N-Acetylmuramic Acid / analogs & derivatives*
  • Uridine Diphosphate N-Acetylmuramic Acid / chemistry
  • Uridine Diphosphate N-Acetylmuramic Acid / metabolism

Substances

  • Enzyme Inhibitors
  • Polyisoprenyl Phosphates
  • Uridine Diphosphate N-Acetylmuramic Acid
  • muramyl-NAc-(pentapeptide)pyrophosphoryl-undecaprenol
  • Bambermycins
  • moenomycin A
  • Glycosyltransferases