Identification of L-methionine oxidation products in tripeptides, in Met-enkephalin and in the bovine basic pancreatic trypsin inhibitor: 1H and 13C NMR study

R. Fruttero, G. Amiconi, F. Ascoli, M. Bolognesi, P. Ascenzi

Research output: Contribution to journalArticlepeer-review

Abstract

L-methionine (Met) oxidation products in tripeptides, in Met-enkephalin and in the bovine basic pancreatic trypsin inhibitor have been identified by 1H and 13C NMR spectroscopy. The oxidation of Met residues by stoichiometric amounts of chloramine-B, H2O2 and I2 yields a mixture of L-methionine sulfoxide (Met(O)) and dehydro-L-methionine (DH-Met), Met(O) and DH-Met, respectively, at pH 7.0 and 25.0°C. The formation of DH-Met occurs only if the amino-group of Met is not derivatized. The analysis of 1H and 13C NMR spectra allows us to quantitate Met oxidation products, to ascertain the relative proportion of the R and S forms of Met(O) and DH-Met, and to reveal the presence of a Met residue at the N-terminal position in peptides and proteins.

Original languageEnglish
Pages (from-to)861-874
Number of pages14
JournalBiochemistry and Molecular Biology International
Volume35
Issue number4
Publication statusPublished - 1995

ASJC Scopus subject areas

  • Biochemistry
  • Genetics
  • Molecular Biology

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