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

Hiroki Shimizu; Jonathan M. Brown; Steven W. Homans; Robert A. Field

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

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

Hiroki Shimizu, Jonathan M. Brown, Steven W. Homans, Robert A. Field

School of Chemistry, Pharmacy and Pharmacology

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

24 Citations (Scopus)

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.

Original language	English
Pages (from-to)	9489-9506
Number of pages	18
Journal	Tetrahedron
Volume	54
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4020(98)00577-8
Publication status	Published - 6 Aug 1998

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title = "Chemical synthesis of 13C-labelled ganglioside Gb3 trisaccharide 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 (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.",

author = "Hiroki Shimizu and Brown, {Jonathan M.} and Homans, {Steven W.} and Field, {Robert A.}",

note = "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.",

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T1 - Chemical synthesis of 13C-labelled ganglioside Gb3 trisaccharide from [U-13C]-D-glucose

AU - Shimizu, Hiroki

AU - Brown, Jonathan M.

AU - Homans, Steven W.

AU - Field, Robert A.

N1 - 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.

PY - 1998/8/6

Y1 - 1998/8/6

N2 - 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.

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 (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.

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

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

M3 - Article

AN - SCOPUS:0032490987

VL - 54

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EP - 9506

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 32

ER -

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

Abstract

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