Synthesis and conformational analysis of the repeating units of bacterial spore peptidoglycan

Carbohydr Res. 2003 Jun 16;338(12):1299-308. doi: 10.1016/s0008-6215(03)00067-3.

Abstract

Deprotection of the fully blocked disacharide allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-beta-D-glucopyranosyl-1',2-lactam)-(1-->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside by selective de-O-allylation and parallel removal of the benzylidene and O-benzyl groups is described. The resulting beta-muramyl lactam-(1-->4)-GlcNAc disaccharide is characterised as the per-O-acetylated derivative by 1H and 13C NMR spectroscopy and X-ray structure analysis. Conformational analysis about glycosidic bond of repeating units of bacterial spore cortex is based on experimental data and molecular modelling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Acetylglucosamine / analogs & derivatives
  • Acetylglucosamine / chemistry
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Glycopeptides / chemical synthesis
  • Glycopeptides / chemistry
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Sequence Data
  • Peptidoglycan / chemistry*
  • Spores, Bacterial / chemistry*
  • X-Ray Diffraction

Substances

  • Glycopeptides
  • Peptidoglycan
  • Acetylglucosamine