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Serendipitous Discovery of Peptide Dialkyl Peroxides
Author(s) -
Moretto Alessandro,
De Zotti Marta,
Scipionato Laura,
Formaggio Fernando,
Crisma Marco,
Toniolo Claudio,
Antonello Sabrina,
Maran Flavio,
Broxterman Quirinus B.
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200210)85:10<3099::aid-hlca3099>3.0.co;2-s
Subject(s) - chemistry , peptide , pyridine , cyclic voltammetry , peroxide , homologous series , combinatorial chemistry , cyclic peptide , stereochemistry , medicinal chemistry , organic chemistry , electrochemistry , biochemistry , electrode
In an attempt to synthesize a homologous series of peptide peresters, we investigated the reaction of the oxazol‐5(4 H )‐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‐IR, 1 H‐NMR, MS, cyclic voltammetry, and X‐ray diffraction. On the basis of the experimental data, a plausible mechanism is proposed for this reaction.