Stepwise synthesis of chitooligosaccharides through a transition-state analogue substrate catalyzed by mutants of chitinase A1 from Bacillus circulans WL-12
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Michinari Kohri
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.
References
Akiyama, K., Kawazu, K., Kobayashi, A. (1995) A novel method for chemo-enzymatic synthesis of elicitor-active chitosan oligomers and partially N-deacetylated chitin oligomers using N-acylated chitotrioses as substrates in a lysozyme-catalyzed transglycosylation reaction system. Carbohydr. Res.279:151–160.10.1016/0008-6215(95)00288-XSearch in Google Scholar
Defaye, J., Gadelle, A., Pedersen, C. (1989) Carbohydrate reactivity in hydrogen-fluoride. 7. Hydrogen fluoride-catalyzed formation of glycoside preparation of methyl 2-acetamido-2-deoxy-β-d-gluco-pyranosides and 2-acetamido-2-deoxy-β-d-galacto-pyranosides, and of β-(1-6)-linked 2-acetamido-2-deoxy-β-d-gluco-pyranosides and 2-acetamido-2-deoxy-β-d-galacto-pyranosides. Carbohydr. Res.186:177–188.Search in Google Scholar
Downie, J.A. (1994) Signaling strategies for nodulation of legumes by Rhizobia. Trends Microbiol.2:318–324.10.1016/0966-842X(94)90448-0Search in Google Scholar
Fukamizo, T. (2000) Chitinolytic enzymes: catalysis, substrate binding, and their application. Curr. Protein Pept. Sci.1:105–124.10.2174/1389203003381450Search in Google Scholar
Hadwiger, L.A. (1999) Host-parasite interactions: elicitation of defense responses in plants with chitosan. In: Chitin and Chitinases. Eds. Jollès, P., Muzzarelli, R.A.A. Birkhäuser Verlag Basel, Switzerland. pp. 185–200.10.1007/978-3-0348-8757-1_13Search in Google Scholar
Hahn, M.G., Bucheli, P., Cervone, F., Doares, S.H., O'Neill, R.A., Darvill, A., Albersheim, P. (1989) Roles of cell wall constituents in plant-pathogen interactions. In: Plant-Microbe Interactions, Vol. 3. Molecular and Genetic Perspectives. Eds. Kosuge, T., Nester, E.W. McGraw-Hill, New York. pp. 131–181.Search in Google Scholar
Honda, Y., Tanimori, S., Kirihata, M., Kaneko, S., Tokuyasu, K., Hashimoto, M., Watanabe, T., Fukamizo, T. (2000) Kinetic analysis of the reaction catalyzed by chitinase A1 from Bacillus circulans WL-12 toward the novel substrate, partially N-deacetylated 4-methylumbelliferyl chitobiosides. FEBS Lett.476:194–197.10.1016/S0014-5793(00)01729-4Search in Google Scholar
Inui, H., Yamaguchi, Y., Hirano, S. (1997) Elicitor actions of N-acetylchitooligosaccharides and laminarioligosaccharides for chitinase and l-phenylalanine ammonia-lyase induction in rice suspension culture. Biosci. Biotechnol. Biochem.61:975–978.10.1271/bbb.61.975Search in Google Scholar
Lipkind, G.M., Shashikov, A.S., Knirrel, Y.A., Vinogradov, E.V., Kochetkov, N.K. (1988) A computer-assisted structural-analysis of regular polysaccharides on the basis of C-13 NMR data. Carbohydr. Res.175:59–75.10.1016/0008-6215(88)80156-3Search in Google Scholar
Shoda, S., Kawasaki, T., Obata, K., Kobayashi, S. (1993) A facile enzymatic synthesis of cellooligosaccharide derivatives using β-lactosyl fluoride. Carbohydr. Res.249:127–137.10.1016/0008-6215(93)84066-FSearch in Google Scholar
Shoda, S., Fujita, M., Lohavisavapanichi, C., Misawa, Y., Ushizaki, K., Tawata, Y., Kuriyama, M., Kohri, M., Kuwata, H., Watanabe, T. (2002a) Efficient method for the elongation of the N-acetylglucosamine unit by combined use of chitinase and β-galactosidase. Helv. Chim. Acta85:3919–3936.10.1002/1522-2675(200211)85:11<3919::AID-HLCA3919>3.0.CO;2-PSearch in Google Scholar
Shoda, S., Izumi, R., Suenaga, M., Saito, K., Fujita, M. (2002b) A facile method for synthesis of 1,2-oxazoline derivative of N-acetylglucosamine promoted by potassium fluoride. Chem. Lett.2:150–151.10.1246/cl.2002.150Search in Google Scholar
Shoda, S., Kohri, M., Kobayashi, A. (2005) Glycosidase-catalyzed synthesis of oligosaccharides through intermediate analogue substrates. In: Biocatalysis: Chemistry and Biology. Ed. Tricone, A. Research Signpost, Kerala. pp. 83–98.Search in Google Scholar
Usui, T., Hayashi, Y., Nanjo, F., Sakai, K., Ishido, Y. (1987) Transglycosylation reaction of a chitinase purified from Nocardia orientalis. Biochim. Biophys. Acta923:302–309.10.1016/0304-4165(87)90017-1Search in Google Scholar
Usui, T., Matsui, H., Isobe, K. (1990) Enzymic synthesis of useful chito-oligosaccharides utilizing transglycosylation by chitinolytic enzymes in a buffer containing ammonium sulfate. Carbohydr. Res.203:65–77.10.1016/0008-6215(90)80046-6Search in Google Scholar
Watanabe, T., Suzuki, K., Oyanagi, W., Ohnishi, K., Tanaka, H. (1990) Gene cloning of chitinase A1 from Bacillus circulans WL-12 revealed its evolutionary relationship to Serratia chitinase and to the type III homology units of fibronectin. J. Biol. Chem.265:15659–15665.10.1016/S0021-9258(18)55449-1Search in Google Scholar
Watanabe, T., Ariga, Y., Sato, U., Toratani, T., Hashimoto, M., Nikaidou, N., Kezuka, Y., Nonaka, T., Sugiyama, J. (2003) Aromatic residues within the substrate-binding cleft of Bacillus circulans chitinase A1 are essential for hydrolysis of crystalline chitin. Biochem. J.376:237–244.10.1042/bj20030419Search in Google Scholar
Yamada, A., Shibuya, N., Kodama, O., Akatsuka, T. (1993) Induction of phytoalexin formation in suspension-cultured rice cells by N-acetyl-chitooligosaccharides. Biosci. Biotech. Biochem.57:405–409.10.1271/bbb.57.405Search in Google Scholar
©2006 by Walter de Gruyter Berlin New York
Articles in the same Issue
- A report from the 2005 Japanese-European Workshop on “Cellulose and Functional Polysaccharides”
- Determination of substituent distribution of viscoses by GPC
- Direct investigation of the structural properties of tension wood cellulose microfibrils using microbeam X-ray fibre diffraction
- Influence of amide content on the crystal structure of chitin
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- Analysis of fragrance compositions of precious coniferous woods grown in Taiwan
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- Dimensional stability and photostability of octanoylated wood
- Measurement of the shear modulus of wood by the square-plate twist method
- Dielectric relaxation of water adsorbed on chemically treated woods
- Influences of drying on internal checking of spruce (Picea abies L.) heat-treated at 212°C
- The role of resol fortifiers in latex wood adhesives
- A simple anisotropy correction procedure for acoustic wood tomography
- Evaluating growth strain of Eucalyptus globulus Labill. from SilviScan measurements
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Articles in the same Issue
- A report from the 2005 Japanese-European Workshop on “Cellulose and Functional Polysaccharides”
- Determination of substituent distribution of viscoses by GPC
- Direct investigation of the structural properties of tension wood cellulose microfibrils using microbeam X-ray fibre diffraction
- Influence of amide content on the crystal structure of chitin
- Stepwise synthesis of chitooligosaccharides through a transition-state analogue substrate catalyzed by mutants of chitinase A1 from Bacillus circulans WL-12
- Synthesis of plantamajoside, a bioactive dihydroxyphenylethyl glycoside from Plantago major L.
- Diffusion of sulfide into Southern pine (Pinus taeda L.) and sweetgum (Liquidambar styraciflua L.) particles and chips
- Laccase-catalysed functionalisation of TMP with tyramine
- Wood liquefaction by ionic liquids
- Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 2: Horseradish peroxidase-catalyzed dehydrogenative polymerization of isoconiferin
- Phenolic compounds in silver birch (Betula pendula Roth) wood
- Analysis of fragrance compositions of precious coniferous woods grown in Taiwan
- Influences of hot pressing temperature and surface structure on VOC emissions from OSB made of Scots pine
- Dimensional stability and photostability of octanoylated wood
- Measurement of the shear modulus of wood by the square-plate twist method
- Dielectric relaxation of water adsorbed on chemically treated woods
- Influences of drying on internal checking of spruce (Picea abies L.) heat-treated at 212°C
- The role of resol fortifiers in latex wood adhesives
- A simple anisotropy correction procedure for acoustic wood tomography
- Evaluating growth strain of Eucalyptus globulus Labill. from SilviScan measurements
- Density assessment of radiata pine: Sampling strategy revisited