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

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 prot...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1996-10, Vol.118 (39), p.9265-9270
Main Authors: Hiruma, Kazumi, Kajimoto, Tetsuya, Weitz-Schmidt, Gabriel, Ollmann, Ian, Wong, Chi-Huey
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9611093