Synthesis of 3-O-β-N-acetylglucosaminyl cyclic tetrasaccharide through a lysozyme-catalyzed transfer reaction

Bioscience, Biotechnology and Biochemistry

Volumn 67, Issue 5, 2003, Pages 1182-1184

  Watanabe, Hikaru ^a   Aga, Hajime ^a   Sonoda, Tomohiko ^a   Kubota, Michio ^a   Fukuda, Shigeharu ^a   Kurimoto, Masashi ^a   Tsujisaka, Yoshio ^a  

^a HAYASHIBARA BIOCHEMICAL LABORATORIES INC   (Japan)

Author keywords

Cyclic tetrasaccharide; Lysozyme; N acetylglucosamine; Transglycosylation

Indexed keywords

CYCLO( 6) GLUCOPYRANOSYL 1 3 GLUCOPYRANOSYL 1 6 (N ACETYLGLUCOSAMINYL 1 3)GLUCOPYRANOSYL 1 3 GLUCOPYRANOSYL (1 ); CYCLO(-6)-GLUCOPYRANOSYL-1-3-GLUCOPYRANOSYL-1-6-(N-ACETYLGLUCOSAMINYL-1-3)GLUCOPYRANOSYL-1-3-GLUCOPYRANOSYL-(1-); DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EGG WHITE; LYSOZYME; OLIGOSACCHARIDE;

AFFINITY CHROMATOGRAPHY; ANIMAL; ARTICLE; CARBOHYDRATE ANALYSIS; CATALYSIS; CHEMISTRY; CHICK EMBRYO; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR GENETICS; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANIMALS; CARBOHYDRATE SEQUENCE; CATALYSIS; CHICK EMBRYO; CHROMATOGRAPHY, AFFINITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EGG WHITE; GLYCOSYLATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; MURAMIDASE; OLIGOSACCHARIDES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 1542440129     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.67.1182     Document Type: Article

References (15)

1. Cote, G. L., and Biely, P., Enzymically produced cyclic a-1,3-linked and a-1,6-linked oligosaccharides of D-glucose. Eur. J. Biochem., 226, 641-648 (1994).
2. Biery, P., Cote, G. L., and Burgess-Cassler, A., Purification and properties of alternanase, a novel endo-a-1,3-a-1,6-D-glucanase. Eur. J. Biochem., 226, 633-639 (1994).
3. Nishimoto, T., Aga, H., Mukai, K., Hashimoto, T., Watanabe, H., Kubota, M., Fukuda, S., Kurimoto, M., and Tsujisaka, Y., Purification and characteriza-tion of glucosyltransferase and glucanotransferase involved in the production of cyclic tetrasaccharide in Bacillus globisporus C11. Biosci. Biotechnol. Biochem., 66, 1806-1818 (2002).
4. Aga, H., Higashiyama, T., Watanabe, H., Sonoda, T., Nishimoto, T., Kubota, M., Fukuda, S., Kurimoto, M., and Tsujisaka, Y., Production of cyclic tetrasaccharide from starch using a novel enzyme system from Bacillus globisporus C11. J. Biosci. Bioeng., 94, 336-342 (2002).
5. Aga, H., Nishimoto, T., Kuniyoshi, M., Maruta, K., Yamashita, H., Higashiyama, T., Nakada, T., Kubota, M., Fukuda, S., Kurimoto, M., and Tsujisaka, Y., 6-a-Glucosyltransferase and 3-a-isomaltosyltransferase from Bacillus globisporus N75. J. Biosci. Bioeng., 95, 215-224 (2003).
6. Bradbrook, G. M., Gessler, K., Cote, G. L., Momany, F., Biery, P., Bordet, P., Perez, S., and Imberty, A., X-ray structure determination and modeling of the cyclic tetrasaccharide cyclo(^-6)-a-D-Glcp-(1 ^ 3)-a-D-Glcp-(1 ^ 6)-a-D-Glcp-(1 ^ 3)-a-D-Glcp-(W. Carbohydr. Res., 329, 655-665 (2000).
7. Nanjo, F., Sakai, K., Ishikawa, M., Isobe, K., and Usui, T., Properties and transglycosylation reaction of a chitinase from Nocardia orientalis. Agric. Biol. Chem., 53, 2189-2195 (1989).
8. Nanjo, F., Ishikawa, M., Katsumi, R., and Sakai, K., Purification, properties, and transglycosylation reaction of b-N-acetylhexosaminidase from Nocardia orientalis. Agric. Biol. Chem., 54, 899-906 (1990).
9. Singh, S., Packwood, J., Samuel, C. J., Critchley, P., and Crout, D. H. G., Glycosidase-catalysed oligosaccharide synthesis: preparation of N-acetyl-chitooligosaccharides using the b-N-acetylhex-osaminidase of Aspergillus oryzae. Carbohydr. Res., 279, 293-305 (1995).
10. Somogyi, S., Notes on sugar determination. J. Biol. Chem., 195, 19-23 (1952).
11. Nelson, N., A photometric adaptation of the Somogyi method for the determination of glucose. J. Biol. Chem., 153, 375-380 (1944).
12. 13C nuclear magnetic resonance spectra of glucobioses, glucotrioses, and glucans. J. Chem. Soc. Perkin Trans.1, 2425-2432 (1973).
13. Chipman, D. M., Pollock, J. J., and Sharon, N., Lysozyme-catalyzed hydrolysis and transglycosylation reaction of bacterial cell wall oligosaccharides. J. Biol. Chem., 243, 487-496 (1968).
14. Matahira, Y., Ohno, K., Kawaguchi, M., Kawagishi, H., and Usui, T., N-Acetylglucosaminyl disaccharide and trisaccharide formation through lysozyme-catalyzed transfer reaction. J. Carbohydr. Chem., 14, 213-225 (1995).
15. Hamayasu, K., Fujita, K., Hara, K., Hashimoto, H., Tanimoto, T., Koizumi, K., Nakano, H., and Kitaha-ta, S., Synthesis of N-acetylglucosaminyl-maltosyl-cyclodexrrin by lysozyme. J. Appl. Glycosci., 46, 445-448 (1999)