A practical one-step synthesis of 1,2-oxazoline derivatives from unprotected sugars and its application to chemoenzymatic β-N- acetylglucosaminidation of disialo-oligosaccharide

Masato Noguchi, Tsukasa Fujieda, Wei Chun Huang, Masaki Ishihara, Atsushi Kobayashi, Shinichiro Shoda

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

A facile and practical method for synthesis of sugar oxazolines (=dihydrooxazoles) from the corresponding N-acetyl-2-amino sugars has been developed by using 2-chloro-1,3-dimethyl-1H-benzimidazol-3-ium chloride (CDMBI) as a dehydrative condensing agent. The intramolecular dehydrative reaction between the 2-acetamido group and the anomeric OH group of unprotected N-acetyl-2-amino sugars took place smoothly in H 2O, leading to the formation of a 1,2-oxazoline (=4,5-dihydrooxazole) moiety in good yield. Since the reaction proceeds in H 2O without using any protecting groups, the resulting oxazolines can be utilized as effective glycosyl donors for the subsequent enzymatic glycosylation. We have successfully demonstrated a highly efficient chemoenzymatic transglycosylation of a disialo-oligosaccharide moiety to p-nitrophenyl N-acetylglucosaminide catalyzed by a mutant endo-N-acetylglucosaminidase without isolating disialo-oligosaccharide oxazoline as synthetic intermediate.

Original languageEnglish
Pages (from-to)1928-1936
Number of pages9
JournalHelvetica Chimica Acta
Volume95
Issue number10
DOIs
Publication statusPublished - 2012 Oct 1

Keywords

  • Oxazoles, 4,5-dihydro-
  • Transglycosylation, chemo-enzymatic
  • β-N-Acetylglucosaminidation

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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