Enzymatic synthesis of fucose-containing disaccharides employing the partially purified alpha-L-fucosidase from Penicillium multicolor.
The alpha-L-Fucp-(1 --> 3)-D-GlcpNAc disaccharide structure is a vital core unit of the oligosaccharide components of glycoconjugates isolated from human milk and blood group substances. Alpha-L-Fucosidase from Penicillium multicolor catalyses the transfer of L-fucose from donor structures such as alpha-L-FucpOpNP and alpha-L-FucpF to various GlcpNAc derivatives and Glcp, forming alpha-(1 --> 3) linkages. The synthesis of several biologically relevant disaccharides including alpha-L-Fucp-(1 --> 3)-alpha-D-GlcpNAcOMe, alpha-L-Fucp-(1 --> 3)-alpha-D-GlcpNAcOAll, alpha-L-Fucp-(1 --> 3)-beta-D-GlcpNAcOAll, alpha-L-Fucp-(1 --> 3)-D-GlcpNAc and alpha-L-Fucp-(1 --> 3)-D-Glcp has been achieved in up to 34% yields by application of this enzyme.
Farkas
E
E
Institute of Organic Chemistry, University of Hamburg, Germany.
Thiem
J
J
Ajisaka
K
K
D000818:Animals; D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000096:biosynthesis* / Q000737:chemistry; D005643:Fucose / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D015394:Molecular Structure; D010407:Penicillium / Q000201:enzymology*; D005644:alpha-L-Fucosidase / Q000302:isolation & purification / Q000378:metabolism*
D004187:Disaccharides; D005643:Fucose; D005644:alpha-L-Fucosidase