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


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.

SUBMITTER: Schlemmer C 

PROVIDER: S-EPMC4498494 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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

Schlemmer Claudine C   Wiebe Christine C   Ferenc Dorota D   Kowalczyk Danuta D   Wedepohl Stefanie S   Ziegelmüller Patrick P   Dernedde Jens J   Opatz Till T  

Chemistry, an Asian journal 20140530 8


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-millimol  ...[more]

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