Oligosaccharide synthesis transglycosylation

Ajisaka K, Eujimoto H, Miyasato M An alpha-L-fucosidase from Penicillium multicolor as a candidate enzyme for the synthesis of a(1 3)-linked fucosyl oligosaccharides by transglycosylation. Carbohydr. Res. 1998 309 125-129. 

In oligosaccharide synthesis via transglycosylation the reaction is kinetically controlled, and the extent of oligosaccharide formation depends on the partition ratio of the glycosyl-enzyme intermediate between the transfer and hydrolytic reaction (Scheme 1). 

Usui, T., Matsui, H., and 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. 

Kanno K, Maeda H, Izumo S, Ikuno M, Takeshita K, Tashiro A, Fujii M (2002) Rapid enzymatic transglycosylation and oligosaccharide synthesis in a microchip reactor. Lab Chip 2 15-18... 

Enzymic synthesis of oligosaccharides by transglycosylation (a) General discussion... 

Murata, T., Hattori, T., Amarume, S., Koichi, A. and Usui, T. (2003). Kinetic studies on endo-beta-galactosidase by a novel colorimetric assay and synthesis of N-acetyllactosamine-repeating oligosaccharide beta-glycosides using its transglycosylation activity. European Journal of Biochemistry, 270, 3709-3719. 

Jack bean a-mannosidase has also been able to catalyze the transglycosylation of rhamnose residue. It has been used in the synthesis of a disaccharide Rhaal,2RhaaSEt in 32.1% yield from RhaapNP and ethyl 1-thio-a-D-rhamnopyranoside. The disaccharide product is a derivative of the common oligosaccharide unit of antigenic lipopolysaccharides from Pseudomonas (33). 

Schmidt D, Sauerbrei B, Thiem J. Chemoenzymatic synthesis of sialyl oligosaccharides with sialidases employing transglycosylation methodology. J. Org. Chem. 2000 65 8518-8526. 

B. Neubacher, S. Scheid, S. Kelm, A. C. C. Frasch, B. Meyer, and J. Thiem, Synthesis of Neu5Ac oligosaccharides and analogues by transglycosylation and their binding properties as ligands to MAG, Chem Bio Chem., 7 (2006) 896-899. 

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