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Rio, Jose C. / Laine, Christiane / Potthast, Antje / Takano, Toshiyuki / Theliander, Hans


International Journal of the Biology, Chemistry, Physics, and Technology of Wood

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Stepwise synthesis of chitooligosaccharides through a transition-state analogue substrate catalyzed by mutants of chitinase A1 from Bacillus circulans WL-12

Michinari Kohri1 / Atsushi Kobayashi2 / Masato Noguchi3 / Shin-ichi Kawaida4 / Takeshi Watanabe5 / Shin-ichiro Shoda6







Corresponding author. Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University, Aoba 6-6-11-514, Aoba-ku, Sendai 980-8579, Japan

Citation Information: Holzforschung. Volume 60, Issue 5, Pages 485–491, ISSN (Online) 1437-434X, ISSN (Print) 0018-3830, DOI: https://doi.org/10.1515/HF.2006.080, August 2006

Publication History

December 19, 2005
May 4, 2006
Published Online:


Several mutants of chitinase A1 from Bacillus circulans WL-12 have been prepared by site-directed mutagenesis of tryptophan 433. The hydrolytic activity of these mutants toward p-nitrophenyl chitobioside was lower than that of wild-type chitinase A1. The mutants were found to catalyze the transglycosylation reaction of the 1,2-oxazoline derivative of N-acetyllactosamine (Gal-GlcNAc-oxa) to N,N′′-diacetylchitobiose (GlcNAc-GlcNAc), giving rise to a transglycosylated tetrasaccharide product (Gal-GlcNAc-GlcNAc-GlcNAc) in high yield. Based on these results, a one-pot synthesis of chitooligosaccharides by combined use of mutant W433Y and β-galactosidase has been demonstrated. By controlling the reaction conditions, chitotriose and chitotetraose were obtained in 74% and 40% yield (determined by HPLC), respectively, without isolating any intermediate products.

Keywords: Bacillus circulans WL-12; chitinase A1; one-pot synthesis; site-directed mutagenesis; sugar oxazoline; transition-state analog substrate; transglycosylation

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