Chemo-enzymatic Synthesis of Novel Oligo-N-acetyllactosamine Derivatives having a β(1-4)–β(1-6) Repeating Unit by Using Transition State Analogue
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| Authors: | Shin-ichiro Shoda Yoshinori Misawa Yousuke Nishijima Yukiko Tawata Tomohiko Kotake Masato Noguchi Atsushi Kobayashi Takeshi Watanabe |
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| Institution: | (1) Department of Biomolecular Engineering, Tohoku University, 6-6-11-514, Aoba, Aoba-ku Sendai, 980-8579, Japan;(2) Department of Applied Biological Chemistry, Faculty of Agriculture, Niigata University, 8050 Ikarashi-2, Niigata 950-2181, Japan |
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| Abstract: | Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1 has been investigated. An extremely rapid hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1 behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulans WL-12). This disaccharide monomer 1 was found to polymerize under basic conditions, giving rise to novel oligosaccharides having a β(1-4)–β(1-6) repeating unit in the main chain. The degree of polymerization of the resulting oligosaccharides was up to 5. This is the first example of enzymatic glycosylation reaction forming a β(1-6) bond catalyzed by chitinase. |
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| Keywords: | Chitinase Enzymatic polyaddition N-acetyllactosamine Oligo-N-acetyllactosaminoglycan 1 2-Oxazoline derivative |
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