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  • Title: Convenient synthesis of beta-(1-->3)-galactosyl disaccharide alpha-glycoside and its analogs as mimic units of mucin-type carbohydrate.
    Author: Murata T, Itoh T, Hayakawa Y, Usui T.
    Journal: J Biochem; 1996 Oct; 120(4):851-5. PubMed ID: 8947852.
    Abstract:
    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.
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