Chemoenzymatic Synthesis of Functional Sialyl LewisX Mimetics with a Heteroaromatic Core. Issue 8 (30th May 2014)

• Record Type: Journal Article
• Authors: Schlemmer, Claudine; Wiebe, Christine; Ferenc, Dorota; Kowalczyk, Danuta; Wedepohl, Stefanie; Ziegelmüller, Patrick; Dernedde, Jens; Opatz, Till
• Is Part Of: Chemistry, an Asian journal. Volume 9:Issue 8(2014:Aug.)
• Page Start: 2119
• Page End: 2125
• Publication Date: 2014-05-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201402118
• Languages: English
• ISSNs: 1861-4728

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>trans</italic>‐sialidase of <italic>Trypanosoma cruzi</italic>. 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.</p> </abstract>