Enzymatic synthesis of alpha-L-fucosyl-N-acetyllactosamines and 3'-O-alpha-L-fucosyllactose utilizing alpha-L-fucosidases.
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.
Murata
T
T
Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University, Japan.
Morimoto
S
S
Zeng
X
X
Watanabe
S
S
Usui
T
T
D000421:Alcaligenes / Q000201:enzymology; D000818:Animals; D002240:Carbohydrate Sequence; D006031:Glycosylation; D016256:Lewis X Antigen / Q000096:biosynthesis*; D008099:Liver / Q000201:enzymology; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000096:biosynthesis*; D013552:Swine; D014312:Trisaccharides / Q000138:chemical synthesis; D005644:alpha-L-Fucosidase / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*
D016256:Lewis X Antigen; D009844:Oligosaccharides; D014312:Trisaccharides; C035714:3'-fucosyllactose; D005644:alpha-L-Fucosidase