The First Total Synthesis of 6-Sulfo-de-N-acetylsialyl Lewis(x) Ganglioside: A Superior Ligand for Human L-Selectin

Originally discovered as a minor by-product of 6-sulfo-N-acetylsialyl Lewis(x) , the de-N-acetylated form 1 is a superior L-selectin ligand to the N-acetyl form. To substantiate the extraordinary reactivity of 1, it was synthesized for the first time and its binding to L-selectin investigated. Compo...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 1999, Vol.38 (8), p.1131-1133
Main Authors: Komba, S, Galustian, C, Ishida, H, Feizi, T, Kannagi, R, Kiso, M
Format: Article
Language:English
Online Access:Get full text
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Summary:Originally discovered as a minor by-product of 6-sulfo-N-acetylsialyl Lewis(x) , the de-N-acetylated form 1 is a superior L-selectin ligand to the N-acetyl form. To substantiate the extraordinary reactivity of 1, it was synthesized for the first time and its binding to L-selectin investigated. Compound 1 and related structures may be high-affinity endogenous ligands for L-selectin that are involved in the interaction of leukocytes with the vascular endothelium.
ISSN:1433-7851
DOI:10.1002/(SICI)1521-3773(19990419)38:8<1131::AID-ANIE1131>3.0.CO;2-B