A novel disaccharide substrate having 1,2-oxazoline moiety for detection of transglycosylating activity of endoglycosidases

Masaya Fujita, Shin ichiro Shoda, Katsuji Haneda, Toshiyuki Inazu, Kaoru Takegawa, Kenji Yamamoto

Research output: Contribution to journalArticle

99 Citations (Scopus)

Abstract

A disaccharide substrate of Manβ1-4GlcNAc-oxazoline 2 was designed and synthesized as a novel probe for detection of the transglycosylating activity of endoglycosidases. A regio- and stereoselective transglycosylation reaction of 2 to GlcNAcβ1-O-pNP or Dns-Asn(GlcNAc)-OH catalyzed by endo-β-N-acetylglucosaminidase from Mucor hiemalis (Endo-M) and endo-β-N-acetylglucosaminidase from Arthrobacter protophormiae (Endo-A) has been demonstrated for the first time, resulting in the core trisaccharide derivative Manβ1-4GlcNAcβ1-4GlcNAcβ1-O-pNP 8 (or -(Dns)Asn-OH). Interestingly, the transglycosylation proceeds irreversibly; the resulting trisaccharide 8 was not hydrolyzed by Endo-M and Endo-A. Based on these results, a new mechanism including an oxazolinium ion intermediate has been proposed for the endoglycosidase-catalyzed hydrolysis or transglycosylation.

Original languageEnglish
Pages (from-to)9-14
Number of pages6
JournalBiochimica et Biophysica Acta - General Subjects
Volume1528
Issue number1
DOIs
Publication statusPublished - Sep 3 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biophysics
  • Biochemistry
  • Molecular Biology

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