Enzymatic transformations in supersaturated substrate solutions: II. Synthesis of disaccharides via transglycosylation

Biotechnology and Bioengineering

Volumn 60, Issue 2, 1998, Pages 197-203

  Millqvist Fureby, Anna ^a   MacManus, David A ^a   Davies, Stephen ^a   Vulfson, Evgeny N ^a  

^a INSTITUTE OF FOOD RESEARCH   (United Kingdom)

Author keywords

Disaccharides; Enzymes; Glycosidases; Glycosides; Regioselectivity; Supersaturated solutions; Synthesis; Transglycosylations

Indexed keywords

BIOCONVERSION; BIOSYNTHESIS; ENZYMES; SUBSTRATES; SUPERSATURATION;

DISACCHARIDES; GLYCOSIDASE; REGIOSELECTIVITY; TRANSGLYCOSYLATION;

POLYSACCHARIDES;

DISACCHARIDE;

ARTICLE; BARLEY; CARBOHYDRATE SYNTHESIS; COFFEE; ENZYME GLYCOSYLATION; ENZYME SUBSTRATE COMPLEX; MOLECULAR INTERACTION; NONHUMAN; SNAIL; STEREOCHEMISTRY;

ALPHA-GALACTOSIDASE; BETA-AMYLASE; CARBOHYDRATE CONFORMATION; COFFEE; DISACCHARIDES; GLYCOSYLATION; HORDEUM; INDICATORS AND REAGENTS; LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; SOLUTIONS; SUBSTRATE SPECIFICITY;

GASTROPODA; HORDEUM VULGARE SUBSP. VULGARE;

EID: 0032552820     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(19981020)60:2<197::AID-BIT7>3.0.CO;2-I     Document Type: Article

References (22)

1. Auge, C., Fernandez-Fernandez, R., Gautheron, C. 1990. The use of immobilised glycosyltransferases in the synthesis of sialyloligosaccharides. Carbohydr. Res. 200: 257-268.
2. Boons, G.-J. 1996. Strategies in oligosaccharide synthesis. Tetrahedron 52: 1095-1121.
3. Crout, D. H. G., MacManus, D. A., Ricca, J. M., Singh, S., Critchley, P., Gibson, W. T. 1992. Biotransformations in the peptide and carbohydrate fields. Pure Appl. Chem. 64: 1079-1084.
4. Fernandez-Mayoralas, A. 1997. Synthesis and modification of carbohydrates using glycosidases and lipases. Top. Curr. Chem. 186: 1-20.
5. Gambert, U., Thiem, J. 1997. Chemical transformations employing glycosyltransferases. Top. Curr. Chem. 186: 21-43.
6. Gijsen, H. J. M., Qiao, L., Fitz, W., Wong, C.-H. 1996. Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics. Chem. Rev. 96: 443-473.
7. Grabowska, U., MacManus, D. A., Biggadike, K., Bird, M. I., Davies, S., Gallagher, T., Hall, L. D., Vulfson, E. N. 1998. Diastereoselective resolution of 6-substituted glycosides via enzymatic hydrolysis. Carbohydr. Res., 305: 351-361.
8. Ichikawa, Y, Liu, J. L. C., Shen, G. J., Wong, C.-H. 1991. Sialyl trisaccharide-in situ generatiom of sialic acid and N-acetyllactosamine coupled with regeneration of UDP-glucose, UDP-galactose, and CMP-sialic acid. J. Am. Chem. Soc. 113: 6300-6302.
9. MacManus, D. A., Grabowska, U., Biggadike, K., Bird, M. I., Davies, S., Gallagher, T., Hall, L. D., Vulfson, E. N. 1998. J. Chem. Soc. Perkin Trans. I, in preparation.
10. Millqvist-Fureby, A., Gill, I. S., Vulfson, E. N. 1997. Enzymatic transformations in supersaturated solutions: I. A general study with glycosidases. Biotechnol. Bioeng. 00: 000-000 (accompanying paper).
11. Nilsson, K. G. I. 1987. A simple strategy for changing the regioselectivity of glycosidase-catalysed formation of disaccharides. Carbohydr. Res. 167: 95-103.
12. Nilsson, K. G. I. 1988. Enzymatic synthesis of oligosaccharides. Trends Biotechnol. 6: 256-264.
13. Palcic, M. M., Hindsgaul, O. 1996. Glycosyltransferases in the synthesis of oligosaccharide analogs. Trends Glycosci. Glycotechnol. 8: 37-49.
14. Svensson, S. C. T., Thiem, J. 1990. Purification of α-L-fucosidase by C-glycosylic affinity chromatography, and the enzymic synthesis of α-L-fucosyl disaccharides. Carbohydr. Res. 200: 391-402.
15. Toshima, K., Tatsuta, K. 1993. Recent progress in O-glycosylation methods and its application to natural products synthesis. Chem. Rev. 93: 1503-1531.
16. Varki, A. 1993. Biological roles of oligosaccharides-all of the theories are correct. Glycobiology 3: 97-130.
17. Vetere, A., Galateo, C., Paoletti, S. 1997. All-aqueous, regiospecific transglycosylation synthesis of 3-O-α-L-fucopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a building block for the synthesis of branched oligosaccharides. Biochem. Biophys. Res. Commun. 234: 358-361.
18. Wang, P. G., Fitz, W., Wong, C.-H. 1995. Making complex carbohydrates via enzymatic routes. CHEMTECH 25: 22-32.
19. Wong, C.-H. 1995. Enzymatic and chemo-enzymatic synthesis of carbohydrates. Pure and Appl. Chem. 67: 1609-1616.
20. Wong, C.-H., Halcomb, R. L., Ichikawa, Y., Kajimoto, T. 1995a. Enzymes in organic synthesis-application to the problems of carbohydrate recognition. 1. Angew. Chem., Int. Ed. Engl. 34: 412-432.
21. Wong, C.-H., Halcomb, R. L., Ichikawa, Y., Kajimoto, T. 1995b. Enzymes in organic synthesis application to the problems of carbohydrate recognition. 2. Angew. Chem., Int. Ed. Engl. 34: 521-546.
22. Zehavi, U., Sharon, N. 1972. The synthesis of methyl 2,4-diacetamido-2,4,6-trideoxy hexopyranosides J. Org. Chem. 37: 2141-2145.