Journal of Applied Glycoscience
Online ISSN : 1880-7291
Print ISSN : 1344-7882
ISSN-L : 1344-7882
Proceedings of the Symposium on Amylases and Related Enzymes, 2008
Synthesis of Spacer-linked Divalent Glycosides by Chitinolytic Enzyme from Amycolatopsis orientalis
Yoshinori MisawaRyuichi MasakaMegumi YanoTakeomi MurataTaichi Usui
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2009 Volume 56 Issue 2 Pages 89-95

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Abstract

Efficient enzymatic synthesis of spacer-linked divalent glycosides, which were designed as glycomimetics, was developed by using transglycosylation of chitinolytic enzyme from Amycolatopsis orientalis. The enzyme catalyzed the synthesis of target divalent glycoside hexan-1,6-diyl bis-(2-acetamido-2-deoxy-β-D-glucopyranoside) (4) through N-acetylglucosaminyl transfer from (GlcNAc)4 to 1,6-hexanediol. When a series of primary diols with different number of carbon atoms were used as acceptor, the corresponding spacer-linked divalent glycosides carrying GlcNAc (1-6) on both sides were obtained. The mechanism of formation of spacer-linked divalent glycosides was further revealed by the enzyme purification. It was specified that N-acetylhexosaminidase itself is directly concerned with transglycosylation of GlcNAc residues to hydroxyl groups on both sides. The interaction of wheat germ agglutinin with a series of spacer-linked divalent glycosides was studied by precipitation analysis and a biosensor based on surface plasmon resonance. Our results demonstrated that a series of spacer-linked divalent glycosides are capable of precipitating WGA as divalent ligands.

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© 2009 by The Japanese Society of Applied Glycoscience
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