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Chemoenzymatic Synthesis of Functional Sialyl Lewis(x) Mimetics With a Heteroaromatic Core

Chemoenzymatic Synthesis of Functional Sialyl Lewis(x) Mimetics With a Heteroaromatic Core

Claudine Schlemmer, Christine Wiebe, Dorota Ferenc, Danuta Kowalczyk, Stefanie Wedepohl, Patrick Ziegelmüller, Jens Dernedde, Till Opatz

Chem Asian J. 2014 Aug;9(8):2119-25.

PMID: 24888318

Abstract:

Functional mimetics of the sialyl Lewis(X) tetrasaccharide were prepared by the enzymatic sialylation of a 1,3-diglycosylated indole and a glycosyl azide, which was subsequently transformed into a 1,4-diglycosylated 1,2,3-triazole, by using the trans-sialidase of Trypanosoma cruzi. These compounds inhibited the binding of E-, L-, and P-selectin-coated nanoparticles to polyacrylamide-bound sialyl-Lewis(X) -containing neighboring sulfated tyrosine residues (sTyr/sLe(X) -PAA) at low or sub-millimolar concentrations. Except for E-selectin, the mimetics showed higher activities than the natural tetrasaccharide.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP92448221	3′-Sialyl-Lewis-a tetrasaccharide		92448-22-1	Price

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