We describe here a rational design and synthesis of
(3-O-carboxymethyl)-β-d-galactopyranosyl
α-d-mannopyranoside which is 5 times as active as sialyl Lewis X in binding
to E-selectin and also effective against P-
and L-selectin. A new method for the 1,1-glycosidic bond formation
via coupling of protected trimethylsilyl
β-d-galactoside and α-mannosyl fluoride in the presence of
BF3·Et2O is described.
This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Le x ), Lewis Y (Le y ), glycopeptides, and sialyl Lewis X (SLe x ) mimetics. Both R-O-fucosyl-L-threonine and R-O-fucosyl-(1R,2R)-2aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLe x mimetics, and some fucopeptides prepared were 5-10 times more active than SLe x as inhibitors of E-selectin.
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