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Journal of Biochemistry Advance Access originally published online on June 13, 2007
Journal of Biochemistry 2007 142(2):239-246; doi:10.1093/jb/mvm125
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© 2007 The Japanese Biochemical Society.

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 and Makoto Ito*

Department of Bioscience and Biotechnology, Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

*To whom correspondence should be addressed: Tel: +81-92-642-2898, Fax: +81-92-642-2907, E-mail: makotoi{at}agr.kyushu-u.ac.jp

Received May 15, 2007; Accepted May 31, 2007


  Abstract

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.

Key Words: endoglycoceramidase, endogalactosylceramidase (EGALC), fluorescent glycosphingolipid, 6-gala series glycosphingolipid, transglycosylation

Abbreviations: BODIPY, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; CDS, ceramide disaccharide, Galß1-6Galß1-1’Cer; CTS, ceramide trisaccharide, Gal{alpha}1-6Galß1-6Galß1-1’Cer; CTeS, ceramide tetrasaccharide, Gal{alpha}1-6Gal{alpha}1-6Galß1-6Galß1-1’Cer; DHB, 2,5-dihydrobenzoic acid; EGALC, endogalactosylceramidase; EGCase, endoglycoceramidase; GalCer, galactosylceramide; GSLs, glycosphingolipids; 6-gala series GSLs, GSLs containing a R-Galß1-6Galß1-1’Cer structure; MALDI-TOF MS, matrix-assisted laser desorption/ionization time of flight mass spectrometry; NBD, 7-nitro-2,1,3-benzoxadiazole; TLC, thin-layer chromatography; TGC, trigalactosylceramide (neogalatriaosylceramide), Galß1-6Galß1-6Galß1-1’Cer


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This article has been cited by other articles:


Home page
 GlycobiologyHome page
Y. Ishibashi, Y. Nagamatsu, S. Meyer, A. Imamura, H. Ishida, M. Kiso, N. Okino, R. Geyer, and M. Ito
Transglycosylation-based fluorescent labeling of 6-gala series glycolipids by endogalactosylceramidase
Glycobiology, July 1, 2009; 19(7): 797 - 807.
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