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Unexpected Reaction Pathway of the Alpha-Aminoalkyl Radical Derived from One-Electron Oxidation of S-Alkylglutathiones.

ABSTRACT: Laser flash photolysis and high-resolution mass spectrometry were used to investigate the mechanism of one-electron oxidation of two S-alkylglutathiones using 3-carboxybenzophenone (3CB) as a photosensitizer. This report indicates an unexpected reaction pathway of the ?-aminoalkyl radical cation (?N+) derived from the oxidation of S-alkylglutathiones. Instead of a common hydrolysis reaction of ?N+ reported earlier for methionine and other sulfur-containing aminoacids and peptides, an intramolecular ring-closure reaction was found for S-alkylglutathiones.

SUBMITTER: Pedzinski T

PROVIDER: S-EPMC7070667 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Unexpected Reaction Pathway of the Alpha-Aminoalkyl Radical Derived from One-Electron Oxidation of S-Alkylglutathiones.

Pedzinski Tomasz T Bobrowski Krzysztof K Marciniak Bronislaw B Filipiak Piotr P

Molecules (Basel, Switzerland) 20200217 4

Laser flash photolysis and high-resolution mass spectrometry were used to investigate the mechanism of one-electron oxidation of two S-alkylglutathiones using 3-carboxybenzophenone (3CB) as a photosensitizer. This report indicates an unexpected reaction pathway of the α-aminoalkyl radical cation (αN+) derived from the oxidation of S-alkylglutathiones. Instead of a common hydrolysis reaction of αN+ reported earlier for methionine and other sulfur-containing ami ...[more]

PMID: 32079230

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