Sugar oxazolines as directly preparable glycosyl donors from unprotected N-Acetyl-2-Amino Sugars: Towards one-pot chemo-enzymatic synthesis of glycoproteins catalyzed by N-acetylglucosaminidases

Shin Ichiro Shoda, Atsushi Kobayashi, Masato Noguchi

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

Sugar oxazolines are transition-state analogue substrates of N-acetylglucosaminidases and act as efficient glycosyl donors for the synthesis of various kinds of glycosyl compounds having N-acetylglucosaminide structures. The direct preparation of sugar oxazolines has been achieved via the intramolecular dehydration reaction of N-acetyl-2-amino sugars by using formamidinium-type dehydrating agents. Various N-acetyl-2-amino sugars were converted to the corresponding oxazoline derivatives in water without using any protecting groups, which makes it possible to demonstrate a one-pot synthesis of N-acetylglucosaminide derivatives without isolating the oxazoline intermediate.

Original languageEnglish
Title of host publicationGlycoscience
Subtitle of host publicationBiology and Medicine
PublisherSpringer Japan
Pages401-407
Number of pages7
ISBN (Electronic)9784431548416
ISBN (Print)9784431548409
DOIs
Publication statusPublished - 2015 Jan 1

Keywords

  • 1H-benzimidazol-3-ium chloride (CDMBI)
  • 2-Chloro-1
  • 2-Chloro-1
  • 3-dimethyl-
  • 3-dimethylimidazolinium chloride (DMC)
  • Chitoheptaose
  • Disialo-oligosaccharide
  • Glycoprotein
  • Glycosylation
  • Intramolecular dehydration
  • N-Acetylglucosaminidase
  • One-pot chemoenzymatic
  • Sugar oxazoline
  • Transition-state analogue substrate

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Medicine(all)

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