Enzymatic transglycosylation of xylose using a glycosynthase.
The application of the hyperactive glycosynthase derived from Agrobacterium sp. beta-glucosidase (AbgE358G-2F6) to the synthesis of xylo-oligosaccharides by using alpha-D-xylopyranosyl fluoride as donor represents the first successful use of glycosynthase technology for xylosyl transfer. Transfer to p-nitrophenyl beta-D-glucopyranoside yields di- and trisaccharide products with beta-(1-->4) linkages in 63% and 35% yields, respectively. By contrast, transfer to p-nitrophenyl beta-D-xylopyranoside yielded the beta-(1-->3) linked disaccharide and beta-D-Xyl-(1-->4)-beta-D-Xyl-(1-->3)-beta-D-Xyl-pNP as major products in 42% and 30% yields, respectively. Transfer of xylose to beta-D-Xyl-(1-->4)-beta-D-Xyl-pNP yielded the beta-(1-->4) linked trisaccharide in 98% yield, thereby indicating that transfers to xylo-disaccharides occur with formation of beta-(1-->4) bonds. Xylosylation of carbamate-protected deoxyxylonojirimycin produced a mixture of di- and tri-'saccharide' products in modest yields.
Kim
Young-Wan
YW
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, Canada V6T 1Z1.
Chen
Hongming
H
Withers
Stephen G
SG
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006031:Glycosylation; D016695:Glycosyltransferases / Q000737:chemistry*; D007700:Kinetics; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012231:Rhizobium / Q000201:enzymology; D013997:Time Factors; D014994:Xylose / Q000737:chemistry* / Q000494:pharmacology; D001617:beta-Glucosidase / Q000737:chemistry*
D009844:Oligosaccharides; D014994:Xylose; D016695:Glycosyltransferases; D006026:Glycoside Hydrolases; D001617:beta-Glucosidase