Synthetic Inhibitors of Cell Adhesion: A Glycopeptide from E-Selectin Ligand 1 (ESL-1) with the Arabino Sialyl Lewis x Structure

Particularly selective methods are required for the synthesis of arabino sialyl Lewis glycopeptides owing to the acid-labile β-arabinopyranoside bond. It is important for the inhibition of cell adhesion that the arabino sialyl Lewis glycopeptide 1, which contains the Gly  -Asp  sequence of the E-sel...

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Published inAngewandte Chemie International Edition Vol. 40; no. 20; p. 3836
Main Authors Rösch, Markus, Herzner, Holger, Dippold, Wolfgang, Wild, Martin, Vestweber, Dietmar, Kunz, Horst
Format Journal Article
LanguageEnglish
Published Germany 15.10.2001
Subjects
glycopeptides
E-selectin ligand
allyl anchor
sialyl Lewisx mimetica
solid-phase synthesis
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Summary:Particularly selective methods are required for the synthesis of arabino sialyl Lewis glycopeptides owing to the acid-labile β-arabinopyranoside bond. It is important for the inhibition of cell adhesion that the arabino sialyl Lewis glycopeptide 1, which contains the Gly  -Asp  sequence of the E-selectin Ligand 1 (ESL-1), binds ten times more strongly than sialyl Lewis to E-selectin, although it is monovalent and does not contain L-fucose, which is considered essential.
ISSN:1521-3773