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Holzforschung

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

Editor-in-Chief: Faix, Oskar

Editorial Board Member: Daniel, Geoffrey / Militz, Holger / Rosenau, Thomas / Salmen, Lennart / Sixta, Herbert / Vuorinen, Tapani / Argyropoulos, Dimitris S. / Balakshin, Yu / Barnett, J. R. / Berry, Richard / Burgert, Ingo / Evans, Robert / Evtuguin, Dmitry V. / Frazier, Charles E. / Fukushima, Kazuhiko / Gellerstedt, Göran / Gindl-Altmutter, Wolfgang / Glasser, W. G. / Heitner, Cyril / Holmbom, Bjarne / Isogai, Akira / Kadla, John F. / Kleen, Marjatta / Koch, Gerald / Lachenal, Dominique / Mansfield, Shawn D. / Morrell, J.J. / Niemz, Peter / Pizzi, Antonio / Ragauskas, Arthur J. / Ralph, John / Rice, Robert W. / Salin, Jarl-Gunnar / Schmitt, Uwe / Schultz, Tor P. / Schwanninger, Manfred / Sipilä, Jussi / Tamminen, Tarja / Viikari, Liisa / Welling, Johannes / Willför, Stefan / Yoshihara, Hiroshi

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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

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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: 10.1515/HF.2006.080, August 2006

Publication History

Received:
December 19, 2005
Accepted:
May 4, 2006
Published Online:
2006-08-16

Abstract

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

References

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