Synthesis and NMR characterization of the trypanosomatid metabolite, N 1,N 8-bis(glutathionyl)spermidine disulphide (trypanothione disulphide)

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.