In an attempt to synthesize a homologous series of peptide peresters, we investigated the reaction of the oxazol-5(4H)-ones of Pht-(Aib)n-OH (n=2-8) and tert-butyl hydroperoxide in the presence of 4-(dimethylamino)pyridine. Unexpectedly, the major product isolated in each case proved to be the peptide dialkyl peroxide. This novel class of peptide derivatives was characterized by FT-IT, NMR, MS, cyclic voltammetry, and X-ray diffraction. On the basis of the experimental data, a plausible mechanism is proposed for this reaction.
Serendipitous discovery of peptide dialkyl peroxides
Crisma M;
2002
Abstract
In an attempt to synthesize a homologous series of peptide peresters, we investigated the reaction of the oxazol-5(4H)-ones of Pht-(Aib)n-OH (n=2-8) and tert-butyl hydroperoxide in the presence of 4-(dimethylamino)pyridine. Unexpectedly, the major product isolated in each case proved to be the peptide dialkyl peroxide. This novel class of peptide derivatives was characterized by FT-IT, NMR, MS, cyclic voltammetry, and X-ray diffraction. On the basis of the experimental data, a plausible mechanism is proposed for this reaction.File in questo prodotto:
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