Abstract

Herein we report a novel and atom-economical route towards an advanced intermediate of a synthetically challenging disaccharide of N-acetylglucosamine (NAG)-N-acetylmuramic (NAM) disaccharide units, linked via [NAG-(β-1,4)-NAM] linkage, the basic carbohydrate skeleton of the bacterial peptidoglycan. A simple synthetic scheme was developed in which a fully protected chitobiose, obtained on a gram scale from chitin, was converted into an advanced precursor of NAG-NAM in 5 steps. The intermediate prepared was obtained from Chitin, a naturally abundant polymer, taking advantage of the chitobiose β-1,4 glycosidic bond, which avoids a difficult step for the disaccharide assembly. This intermediate constitutes of a versatile scaffold that allows further derivatization, with impact in the glycobiology field.

Original languageEnglish
Pages (from-to)2544-2551
Number of pages8
JournalAsian Journal of Organic Chemistry
Volume7
Issue number12
DOIs
Publication statusPublished - 1 Dec 2018

Keywords

  • acetylglucosamine
  • chitin
  • chitooligosaccharides
  • NAG-NAM
  • regioselective protection

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