title: 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.
authors.affiliation: Institut für Organische Chemie, Johannes Gutenberg-Universität, Duesbergweg 10-14, 55128 Mainz (Germany), Fax: (+49) 6131-3922338.
authors.forename: Claudine
authors.initials: C
authors.lastname: Schlemmer
authors.forename: Christine
authors.initials: C
authors.lastname: Wiebe
authors.forename: Dorota
authors.initials: D
authors.lastname: Ferenc
authors.forename: Danuta
authors.initials: D
authors.lastname: Kowalczyk
authors.forename: Stefanie
authors.initials: S
authors.lastname: Wedepohl
authors.forename: Patrick
authors.initials: P
authors.lastname: Ziegelmüller
authors.forename: Jens
authors.initials: J
authors.lastname: Dernedde
authors.forename: Till
authors.initials: T
authors.lastname: Opatz
mesh_terms: D000818:Animals; D002240:Carbohydrate Sequence; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D006023:Glycoproteins / Q000737:chemistry*; D018716:Molecular Mimicry; D008969:Molecular Sequence Data; D009439:Neuraminidase / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D019087:Selectins / Q000737:chemistry; D000080506:Sialyl Lewis X Antigen; D021241:Spectrometry, Mass, Electrospray Ionization; D014349:Trypanosoma cruzi / Q000201:enzymology
chemical_list: D006023:Glycoproteins; D009844:Oligosaccharides; D019087:Selectins; D000080506:Sialyl Lewis X Antigen; C069715:trans-sialidase; D009439:Neuraminidase
keywords: cell adhesion; enzyme catalysis; heterocycles; oligosaccharides; saccharide mimetics