Synthesis of spacer-linked divalent glycosides by chitinolytic enzyme from Amycolatopsis orientalis
2009
Misawa, Y.(Yaizu Suisankagaku Industry Co. Ltd., Shizuoka (Japan)) | Masaka, R. | Yano, M. | Murata, T. | Usui, T.
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-beta-D-glucopyranoside) (4) through N-acetylglucosaminyl transfer from (GlcNAc)sub(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 is capable of precipitating WGA as divalent ligands.
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