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 journalArticle

21 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)911-914
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number4
StatePublished - 1990
Externally publishedYes

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Spermidine
Metabolites
Disulfides
Nuclear magnetic resonance
Chemical shift
Nuclear magnetic resonance spectroscopy
Protons
Peptides
trypanothione

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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AU - Glushka, John

AU - Cowburn, David

AU - Cerami, Anthony

PY - 1990

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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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