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

Particularly selective methods are required for the synthesis of arabino sialyl Lewisx glycopeptides owing to the acid‐labile β‐arabinopyranoside bond. It is important for the inhibition of cell adhesion that the arabino sialyl Lewisx glycopeptide 1, which contains the Gly 672–Asp 681 sequence of th...

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Published inAngewandte Chemie (International ed.) Vol. 40; no. 20; pp. 3836 - 3839
Main Authors Rösch, Markus, Herzner, Holger, Dippold, Wolfgang, Wild, Martin, Vestweber, Dietmar, Kunz, Horst
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 15.10.2001
WILEY‐VCH Verlag GmbH
Subjects
allyl anchor
E-selectin ligand
glycopeptides
sialyl Lewisx mimetica
solid-phase synthesis
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Summary:Particularly selective methods are required for the synthesis of arabino sialyl Lewisx glycopeptides owing to the acid‐labile β‐arabinopyranoside bond. It is important for the inhibition of cell adhesion that the arabino sialyl Lewisx glycopeptide 1, which contains the Gly 672–Asp 681 sequence of the E‐selectin Ligand 1 (ESL‐1), binds ten times more strongly than sialyl Lewisx to E‐selectin, although it is monovalent and does not contain L‐fucose, which is considered essential.
Bibliography:ArticleID:ANIE3836
ark:/67375/WNG-PQ0BRMZW-W
istex:F021CFE94CAA8D9EE7F5553683EC80B1B6A4E1E9
This work was supported by the Deutsche Forschungsgemeinschaft and by the Fonds der Chemischen Industrie
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ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20011015)40:20<3836::AID-ANIE3836>3.0.CO;2-5