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Chemoenzymatic Synthesis of Functional Sialyl Lewis X Mimetics with a Heteroaromatic Core
Author(s) -
Schlemmer Claudine,
Wiebe Christine,
Ferenc Dorota,
Kowalczyk Danuta,
Wedepohl Stefanie,
Ziegelmüller Patrick,
Dernedde Jens,
Opatz Till
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402118
Subject(s) - tetrasaccharide , chemistry , sialyl lewis x , stereochemistry , azide , glycosyl , biochemistry , glycan , tyrosine , glycosyltransferase , enzyme , selectin , organic chemistry , glycoprotein , polysaccharide , adhesion
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.