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Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin

1996; American Chemical Society; Volume: 118; Issue: 39 Linguagem: Inglês

10.1021/ja9611093

1943-2984

Kazumi Hiruma, Tetsuya Kajimoto, Gabriel Wéitz-Schmidt, Ian R. Ollmann, Chi‐Huey Wong,

Cell Adhesion Molecules Research

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.