Synthesis of the NAG-NAM disaccharide via a versatile intermediate

Ramu Enugala, Marina J. D. Pires, Maria Manuel Martinho Sequeira Barata Marques

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

A simple strategy for the synthesis of a alpha-GlcNAc-(1 -> 4)-MurNAc (NAG-NAM) moiety, crucial for the preparation of synthetic components of a bacterial peptidoglycan, was achieved. This strategy relies on the use of three O-protecting groups, 4,6-O-benzilidene acetal, benzyl, and acetyl group, which allows further regioselective manipulation at O-3, O-4 positions, and on the insertion of the peptide chain at the lactate moiety in an advanced and versatile intermediate. Overall, a simple route to achieve the biological relevant NAG-NAM is presented, which may serve as a conceptual framework in the designing of synthetic strategies of different natural and non-natural polysaccharides. (C) 2013 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)112-118
Number of pages7
JournalCarbohydrate Research
Volume384
DOIs
Publication statusPublished - 30 Jan 2014

Keywords

  • N-Acetyl glucosamine
  • NAG-NAM
  • Protecting group
  • Glycosylation
  • Peptidoglycan
  • BACTERIAL-CELL WALL
  • ALLYL ETHERS
  • CARBOHYDRATE-CHEMISTRY
  • ESCHERICHIA-COLI
  • PROTECTING GROUP
  • LIPID-IV
  • PEPTIDOGLYCAN
  • GLUCOSAMINE
  • PALLADIUM
  • ALCOHOLS

Fingerprint

Dive into the research topics of 'Synthesis of the NAG-NAM disaccharide via a versatile intermediate'. Together they form a unique fingerprint.

Cite this