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Chemoenzymatic synthesis of functional sialyl Lewis(x) mimetics with a heteroaromatic core.

Chemistry, an Asian journal (2014-06-04)
Claudine Schlemmer, Christine Wiebe, Dorota Ferenc, Danuta Kowalczyk, Stefanie Wedepohl, Patrick Ziegelmüller, Jens Dernedde, Till Opatz
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.

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