Regioselective transglycosylation in the synthesis of oligosaccharides: comparison of beta-galactosidases and sialidases of various origins.
N-Acetyl-lactosamine(beta-D-Gal p-(1-->4)-D-Glc pNAc) was synthesized regioselectively with the aid of the transglycosylation activity of beta-galactosidase isolated from Diplococcus pneumoniae using p-nitrophenyl beta-D-galactopyranoside as the donor. Also, transglycosylation of the sialyl group in an alpha-(2-->8)-linked sialic acid dimer or p-nitrophenyl glycoside of sialic acid to N-acetyl-lactosamine was performed using sialidases of various origins. When sialidase from Clostridium perfringens, Arthrobacter ureafaciens, or Vibrio cholerae was used, alpha-(2-->6)-linked sialyl N-acetyl-lactosamine was obtained regioselectively. In contrast, when sialidase from newcastle disease virus was used, the alpha-(2-->3)-linked isomer was obtained regioselectively. The regioselectivity of the transglycosylation reaction using beta-galactosidase and sialidase was compared with hydrolysis specificity toward the same linkages.
Ajisaka
K
K
Meiji Institute of Health Science, Meiji Milk Products Co., Ltd., Odawara, Japan.
Fujimoto
H
H
Isomura
M
M
D000606:Amino Sugars / Q000138:chemical synthesis / Q000737:chemistry; D001173:Arthrobacter / Q000201:enzymology; D001236:Aspergillus oryzae / Q000201:enzymology; D001407:Bacillus / Q000201:enzymology; D001419:Bacteria / Q000201:enzymology*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003016:Clostridium perfringens / Q000201:enzymology; D004926:Escherichia coli / Q000201:enzymology; D006031:Glycosylation; D007700:Kinetics; D008969:Molecular Sequence Data; D009439:Neuraminidase / Q000378:metabolism*; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000138:chemical synthesis*; D013296:Streptococcus pneumoniae / Q000201:enzymology; D014734:Vibrio cholerae / Q000201:enzymology; D001616:beta-Galactosidase / Q000378:metabolism*
D000606:Amino Sugars; D009844:Oligosaccharides; C000458:N-acetyllactosamine; D009439:Neuraminidase; D001616:beta-Galactosidase