Synthesis and NMR characterization of the trypanosomatid metabolite, N 1,N8-bis(glutathionyl)spermidine disulphide (trypanothione disulphide)

Graeme B. Henderson; John Glushka; David Cowburn; Anthony Cerami

doi:10.1039/p19900000911

Synthesis and NMR characterization of the trypanosomatid metabolite, N ¹,N⁸-bis(glutathionyl)spermidine disulphide (trypanothione disulphide)

Graeme B. Henderson
, John Glushka
, David Cowburn
, Anthony Cerami

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

22 Scopus citations

Abstract

An optimized chemical synthesis of the novel trypanosomatid metabolite, N¹,N⁸-bis(glutathionyl)-spermidine(trypanothione disulphide) is described, and its solution structure has been investigated by NMR spectroscopy. The ¹H, ¹³C, and ¹⁵N chemical shifts, as well as proton NOE data are compatible with two similar extended peptide segments connected by a flexible spermidine chain. The data do not support a predominant β sheet structure but indicate considerable flexibility in aqueous solution.

Original language	English
Pages (from-to)	911-914
Number of pages	4
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	4
DOIs	https://doi.org/10.1039/p19900000911
State	Published - 1990
Externally published	Yes

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title = "Synthesis and NMR characterization of the trypanosomatid metabolite, N 1,N8-bis(glutathionyl)spermidine disulphide (trypanothione disulphide)",

abstract = "An optimized chemical synthesis of the novel trypanosomatid metabolite, N1,N8-bis(glutathionyl)-spermidine(trypanothione disulphide) is described, and its solution structure has been investigated by NMR spectroscopy. The 1H, 13C, and 15N chemical shifts, as well as proton NOE data are compatible with two similar extended peptide segments connected by a flexible spermidine chain. The data do not support a predominant β sheet structure but indicate considerable flexibility in aqueous solution.",

author = "Henderson, \{Graeme B.\} and John Glushka and David Cowburn and Anthony Cerami",

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AU - Henderson, Graeme B.

AU - Glushka, John

AU - Cowburn, David

AU - Cerami, Anthony

PY - 1990

Y1 - 1990

N2 - An optimized chemical synthesis of the novel trypanosomatid metabolite, N1,N8-bis(glutathionyl)-spermidine(trypanothione disulphide) is described, and its solution structure has been investigated by NMR spectroscopy. The 1H, 13C, and 15N chemical shifts, as well as proton NOE data are compatible with two similar extended peptide segments connected by a flexible spermidine chain. The data do not support a predominant β sheet structure but indicate considerable flexibility in aqueous solution.

AB - An optimized chemical synthesis of the novel trypanosomatid metabolite, N1,N8-bis(glutathionyl)-spermidine(trypanothione disulphide) is described, and its solution structure has been investigated by NMR spectroscopy. The 1H, 13C, and 15N chemical shifts, as well as proton NOE data are compatible with two similar extended peptide segments connected by a flexible spermidine chain. The data do not support a predominant β sheet structure but indicate considerable flexibility in aqueous solution.

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DO - 10.1039/p19900000911

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ER -

Synthesis and NMR characterization of the trypanosomatid metabolite, N 1,N8-bis(glutathionyl)spermidine disulphide (trypanothione disulphide)

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Synthesis and NMR characterization of the trypanosomatid metabolite, N ¹,N⁸-bis(glutathionyl)spermidine disulphide (trypanothione disulphide)