Convenient synthesis of beta-(1-->3)-galactosyl disaccharide alpha-glycoside and its analogs as mimic units of mucin-type carbohydrate.
beta-Galactosidase from porcine testes induced regioselective transglycosylation from lactose to the 3-position of 2-acetamido glycosides. When alpha-D-GalNAc-OC6H4NO2-p was used as an acceptor, the enzyme synthesized mainly beta-D-Gal-(1-->3)-alpha-D-GalNAc-OC6H4NO2-p with its (1-->6) linked isomer. The use of an inclusion complex of the glycoside acceptor with beta-CD increased the efficiency of transglycosylation by increasing the solubility of the acceptor. In the same way, the use of beta-D-GalNAc-OC6H4NO2-p as acceptor led to the preferential synthesis of beta-D-Gal-(1-->3)-beta-D-GalNAc-OC6H4NO2-p over that of its (1-->6) linked isomer. beta-D-Gal-(1.3)-beta-D-GlcNAc-OC6H4NO2-p was also synthesized with beta-D-GlcNAc-OC6H4NO2-p acceptor by the consecutive use of beta-D-galactosidases from porcine testes and Bacillus circulans. These enzyme reactions are efficient enough to allow the one-pot preparation of the desired disaccharide glycosides.
Murata
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T
Faculty of Agriculture, Department of Applied Biological Chemistry, Shizuoka University.
Itoh
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T
Hayakawa
Y
Y
Usui
T
T
D000421:Alcaligenes / Q000201:enzymology; D000818:Animals; D003505:Cyclodextrins; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006596:Hexosaminidases / Q000737:chemistry; D008297:Male; D009077:Mucins / Q000737:chemistry*; D009598:Nitrophenylgalactosides; D013379:Substrate Specificity; D013552:Swine; D013737:Testis / Q000201:enzymology; D048809:alpha-N-Acetylgalactosaminidase; D047392:beta-Cyclodextrins; D001616:beta-Galactosidase / Q000737:chemistry*
D003505:Cyclodextrins; D006027:Glycosides; D009077:Mucins; D047392:beta-Cyclodextrins; D009598:Nitrophenylgalactosides; D006596:Hexosaminidases; D001616:beta-Galactosidase; D048809:alpha-N-Acetylgalactosaminidase; C031215:betadex