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Biological Chemistry

Editor-in-Chief: Brüne, Bernhard

Editorial Board: Buchner, Johannes / Lei, Ming / Ludwig, Stephan / Thomas, Douglas D. / Turk, Boris / Wittinghofer, Alfred


IMPACT FACTOR 2018: 3.014
5-year IMPACT FACTOR: 3.162

CiteScore 2018: 3.09

SCImago Journal Rank (SJR) 2018: 1.482
Source Normalized Impact per Paper (SNIP) 2018: 0.820

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1437-4315
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Volume 382, Issue 2

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6-O-Sulfo De-N-Acetylsialyl Lewis X as a Novel High-Affinity Ligand for Human L-Selectin: Total Synthesis and Structural Characterization

Shiro Komba / Masanori Yamaguchi / Hideharu Ishida / Makoto Kiso
Published Online: 2005-06-01 | DOI: https://doi.org/10.1515/BC.2001.030

Abstract

Total synthesis and structural characterization of a novel 6-Osulfo deNacetylsialyl Lewis X, which was originally discovered as a minor byproduct of the parent 6-Osulfo Nacetylsialyl Lewis X, a highaffinity endogenous ligand for human Lselectin, are described. The total synthesis has been achieved by a highly efficient, regio and α stereoselective glycosylation of Ntrifluoroacetylneuraminic acid, selective protections of the 3- and 6-hydroxyl groups of Nacetylglucosamine that undergo fucosylation and sulfation, and construction of the glycolipid structure containing a ceramide. The structure of 6-Osulfo deNacetylsialyl Lewis X ganglioside was characterized by fast atom bombardment mass spectrometry (FABMS).

About the article

Published Online: 2005-06-01

Published in Print: 2001-02-12


Citation Information: Biological Chemistry, Volume 382, Issue 2, Pages 233–240, ISSN (Print) 1431-6730, DOI: https://doi.org/10.1515/BC.2001.030.

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