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Carbohydr Res. 1999 Aug 15;320(3-4):192-9.

Enzymatic synthesis of alpha-L-fucosyl-N-acetyllactosamines and 3'-O-alpha-L-fucosyllactose utilizing alpha-L-fucosidases.

Author information

1
Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University, Japan.

Abstract

An alpha-L-fucosidase from porcine liver produced alpha-L-Fuc-(1-->2)-beta-D-Gal-(1-->4)-D-GlcNAc (2'-O-alpha-L-fucosyl-N-acetyllactosamine, 1) together with its isomers alpha-L-Fuc-(1-->3)-beta-D-Gal-(1-->4)-D-GlcNAc (2) and alpha-L-Fuc-(1-->6)-beta-D-Gal-(1-->4)-D-GlcNAc (3) through a transglycosylation reaction from p-nitrophenyl alpha-L-fucopyranoside and beta-D-Gal-(1-->4)-D-GlcNAc. The enzyme formed the trisaccharides 1-3 in 13% overall yield based on the donor, and in the ratio of 40:37:23. In contrast, transglycosylation by Alcaligenes sp. alpha-L-fucosidase led to the regioselective synthesis of trisaccharides containing a (1-->3)-linked alpha-L-fucosyl residue. When beta-D-Gal-(1-->4)-D-GlcNAc and lactose were acceptors, the enzyme formed regioselectively compound 2 and alpha-L-Fuc-(1-->3)-beta-D-Gal-(1-->4)-D-Glc (3'-O-alpha-L-fucosyllactose, 4), respectively, in 54 and 34% yields, based on the donor.

PMID:
10573857
DOI:
10.1016/s0008-6215(99)00156-1
[Indexed for MEDLINE]

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