A facile enzymatic synthesis of cellooligosaccharide derivatives using beta-lactosyl fluoride.
A convenient method for the preparation of cellooligosaccharide derivatives has been developed that uses beta-lactosyl fluoride as the glycosyl donor. The reaction consists of the following enzymatic processes; (1) a cellulase-catalyzed regio- and stereo-selective lactosylation of a beta-cellobioside as the glycosyl acceptor, utilizing the transglycosylating ability of an enzyme-substrate complex formed from beta-lactosyl fluoride and cellulase; (2) beta-D-galactosidase-catalyzed regioselective cleavage of the terminal D-galactose unit from the lactosylated product, giving rise to a beta-cellotrioside derivative. A cellotetraoside derivative has successfully been prepared in a stereo- and regio-selective manner by repeating these enzymatic reactions and using the resulting beta-cellotrioside as starting material.
Shoda
S
S
Department of Molecular Chemistry and Engineering, Faculty of Engineering, Tohoku University, Sendai, Japan.
Kawasaki
T
T
Obata
K
K
Kobayashi
S
S
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002480:Cellulase / Q000378:metabolism; D002482:Cellulose; D007202:Indicators and Reagents; D007785:Lactose / Q000031:analogs & derivatives*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D001616:beta-Galactosidase / Q000378:metabolism
D007202:Indicators and Reagents; D009844:Oligosaccharides; C084793:lactosyl fluoride; D002482:Cellulose; D001616:beta-Galactosidase; D002480:Cellulase; D007785:Lactose