Chemical synthesis of 13C-labelled ganglioside Gb3 trisaccharide from [U-13C]-D-glucose

Shimizu, Hiroki, Brown, Jonathan M., Homans, Steven W. and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (1998) Chemical synthesis of 13C-labelled ganglioside Gb3 trisaccharide from [U-13C]-D-glucose. Tetrahedron, 54 (32). pp. 9489-9506. ISSN 0040-4020

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Abstract

The interaction of bacterial toxins with their cell surface glycolipid receptors offers scope for therapeutic intervention. Whilst crystal and solution structures of Escherichia coli verotoxin-1 have been reported, the precise nature of the interaction of the glycolipid binding domain of the toxin with its natural ligand, ganglioside Gb3 (Ga1α1→4Ga1β1→4Glcβ1→Cer), remain to be confirmed. To this end we now report the synthesis of the (2-trimethylsilyl)ethyl glycoside of the Gb3 trisaccharide in isotopically enriched form from [U-13C]-D-glucose.

Item Type: Article
Additional Information: Funding Information: We acknowledge the BBSRC for providing financial support. Dr. T. J. Rutherford and Mrs. M. H. Smith are thanked for assistance with NMR spectroscopy, Mrs. S. Williamson for assistance with microanalysis and Mr. C. Millar and for assistance with in-house mass spectromerty. We also thank Dr J.A. Ballantine and colleagues at the EPSRC Mass Spectrometry Service Centre, Swansea.
Uncontrolled Keywords: biochemistry,drug discovery,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School: Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
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Depositing User: LivePure Connector
Date Deposited: 11 Sep 2024 09:30
Last Modified: 25 Sep 2024 18:09
URI: https://ueaeprints.uea.ac.uk/id/eprint/96695
DOI: 10.1016/S0040-4020(98)00577-8

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