Chemical synthesis of13C-labelled ganglioside Gb3trisaccharide from [U-13C]-D-glucose

H. Shimizu; J.M. Brown; S.W. Homans; R.A. Field

doi:10.1016/S0040-4020(98)00577-8

Chemical synthesis of¹³C-labelled ganglioside Gb3trisaccharide from [U-¹³C]-D-glucose

H. Shimizu, J.M. Brown, S.W. Homans, R.A. Field

Research output: Contribution to journal › Article › peer-review

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 (Galα1 →4Galβ1 →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.

Original language	Undefined
Pages (from-to)	9489-9506
Number of pages	18
Journal	Tetrahedron
DOIs	https://doi.org/10.1016/S0040-4020(98)00577-8
Publication status	Published - 1998

Research Beacons, Institutes and Platforms

Manchester Institute of Biotechnology

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10.1016/S0040-4020(98)00577-8

Cite this

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title = "Chemical synthesis of13C-labelled ganglioside Gb3trisaccharide from [U-13C]-D-glucose",

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 (Galα1 →4Galβ1 →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.",

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year = "1998",

doi = "10.1016/S0040-4020(98)00577-8",

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journal = "Tetrahedron",

issn = "0040-4020",

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T1 - Chemical synthesis of13C-labelled ganglioside Gb3trisaccharide from [U-13C]-D-glucose

AU - Shimizu, H.

AU - Brown, J.M.

AU - Homans, S.W.

AU - Field, R.A.

PY - 1998

Y1 - 1998

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AB - 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 (Galα1 →4Galβ1 →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.

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U2 - 10.1016/S0040-4020(98)00577-8

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EP - 9506

JO - Tetrahedron

JF - Tetrahedron