Synthesis of mannopyranose disaccharides as photoaffinity probes for mannosyltransferases in Mycobacterium tuberculosis

Carbohydr Res. 2004 Feb 25;339(3):683-91. doi: 10.1016/j.carres.2003.10.031.

Abstract

Mannosyltransferases play a crucial role in mycobacterial cell-wall biosynthesis and are potential new drug targets for the treatment of tuberculosis. Herein, we describe the synthesis of alpha-(1-->2)- and alpha-(1-->6)-linked mannopyranosyl disaccharides possessing a 5-azidonaphthlene-1-sulfonamidoethyl group as photoaffinity probes for active-site labeling studies of mannosyltransferases in Mycobacterium tuberculosis.

Publication types

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

MeSH terms

  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Disaccharides / metabolism
  • Mannose / chemical synthesis*
  • Mannose / chemistry
  • Mannose / metabolism
  • Mannosyltransferases / analysis*
  • Mannosyltransferases / chemistry
  • Mannosyltransferases / metabolism
  • Molecular Structure
  • Mycobacterium tuberculosis / enzymology
  • Photoaffinity Labels / analysis*
  • Photoaffinity Labels / chemical synthesis*
  • Photoaffinity Labels / chemistry
  • Photoaffinity Labels / metabolism
  • Structure-Activity Relationship

Substances

  • Disaccharides
  • Photoaffinity Labels
  • Mannosyltransferases
  • Mannose