Synthesis of fluorescent glycosphingolipids and neoglycoconjugates which contain 6-gala oligosaccharides using the transglycosylation reaction of a novel endoglycoceramidase (EGALC)

Yohei Ishibashi, Masashi Kiyohara, Nozomu Okino, Makoto Ito

研究成果: Contribution to journalArticle査読

9 被引用数 (Scopus)

抄録

Endoglycoceramidase is a glycohydrolase capable of hydrolysing the O-glycosidic linkage between oligosaccharides and ceramides of various glycosphingolipids. However, no endoglycoceramidase reported so far can hydrolyse 6-gala series glycosphingolipids which possess the common structure R-Galß1-6Galß1-1'Cer. Recently, we found a novel endoglycoceramidase (endogalactosylceramidase, EGALC) which specifically hydrolyses 6-gala series glycosphingolipids. Here, we report that EGALC catalyses the hydrolysis as well as transglycosylation. An intact sugar chain of neogalatriaosylceramide (Galß1-6Galß1-6Galß1-1'Cer) was found to be transferred by EGALC to a primary hydroxyl group of various alkanols and non-ionic detergents such as Triton X-100 generating corresponding alkyl- and Triton- trigalactooligosaccharides. Furthermore, fluorescent 6-gala series glycosphingolipids were synthesized by transglycosylation in a reaction with EGALC using fluorescent ceramides as acceptors. Because of high efficiency and broad acceptor specificity, EGALC would facilitate the synthesis of fluorescent glycosphingolipids and neoglycoconjugates which contain 6-gala oligosaccharides.

本文言語英語
ページ(範囲)239-246
ページ数8
ジャーナルJournal of biochemistry
142
2
DOI
出版ステータス出版済み - 8 2007

All Science Journal Classification (ASJC) codes

  • 生化学
  • 分子生物学

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