To make a glycoprotein with a definite molecular weight

Shin Ichiro Shoda, Atsushi Kobayashi, Masato Noguchi

Research output: Contribution to journalReview articlepeer-review

1 Citation (Scopus)

Abstract

Glycoproteins, naturally occurring hybrid macromolecules composed of a protein and oligosaccharide chains, show various important biological activities in medical and pharmaceutical sciences. In spite of strong demand for glycoproteins having a definite structure, its specific preparation is still an unsolved problem in the field of synthetic organic chemistry. Here we propose an efficient strategy for synthesis of glycoproteins via 1,2-oxazoline derivatives as glycosyl donors for enzymatic transglycosylation. We developed a facile method for synthesis of sugar oxazoline derivatives by the intramolecular dehydration reaction of the corresponding unprotected 2-acetamido-sugars in water using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a dehydrating agent. According to this method, disialo-oligosaccharides can be converted to the corresponding 1,2-oxazoline derivatives in high yields without protecting the hydroxy groups. A transglycosylation of the resulting oxazoline derivative to the GlcNAc moiety on a protein has successfully been demonstrated catalyzed by a mutant of A'-acetylglucosaminidase-M, giving rise to a monodispersed disialo-type glycoprotein.

Original languageEnglish
Pages (from-to)1252-1258
Number of pages7
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume71
Issue number12
DOIs
Publication statusPublished - 2013

Keywords

  • Dehydrating agent
  • Direct anomeric activation
  • Disialo-oligosaccharide
  • Enzymatic glycosylation
  • Glycoprotein
  • N-acetylglucosaminidase
  • Sugar oxazoline
  • Transition state analogue substrate

ASJC Scopus subject areas

  • Organic Chemistry

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