Chemo-enzymatic Synthesis of Novel Oligo-N-acetyllactosamine Derivatives having a β(1-4)–β(1-6) Repeating Unit by Using Transition State Analogue Substrate

Autor: Shoda, Shin-ichiro, Misawa, Yoshinori, Nishijima, Yousuke, Tawata, Yukiko, Kotake, Tomohiko, Noguchi, Masato, Kobayashi, Atsushi, Watanabe, Takeshi
Zdroj: Cellulose; August 2006, Vol. 13 Issue: 4 p477-484, 8p
Abstrakt: Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1has been investigated. An extremely rapid hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulansWL-12). This disaccharide monomer 1was 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.Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1has been investigated. An extremely rapid hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulansWL-12). This disaccharide monomer 1was 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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