Unexpected Reaction Pathway of the Alpha-Aminoalkyl Radical Derived from One-Electron Oxidation of <i>S</i>-Alkylglutathiones

Unexpected Reaction Pathway of the Alpha-Aminoalkyl Radical Derived from One-Electron Oxidation of <i>S</i>-Alkylglutathiones

Laser flash photolysis and high-resolution mass spectrometry were used to investigate the mechanism of one-electron oxidation of two <i>S</i>-alkylglutathiones using 3-carboxybenzophenone (3CB) as a photosensitizer. This report indicates an unexpected reaction pathway of the &#945;-a...

Full description

Bibliographic Details
Main Authors: Tomasz Pedzinski, Krzysztof Bobrowski, Bronislaw Marciniak, Piotr Filipiak
Format: Article
Language:English
Published: MDPI AG 2020-02-01
Series:Molecules
Subjects:
<i>s</i>-alkylglutathiones
one-electron oxidation
laser flash photolysis
decarboxylation
Online Access:https://www.mdpi.com/1420-3049/25/4/877
Description
Summary:Laser flash photolysis and high-resolution mass spectrometry were used to investigate the mechanism of one-electron oxidation of two <i>S</i>-alkylglutathiones using 3-carboxybenzophenone (3CB) as a photosensitizer. This report indicates an unexpected reaction pathway of the &#945;-aminoalkyl radical cation (&#945;N<sup>+</sup>) derived from the oxidation of <i>S</i>-alkylglutathiones. Instead of a common hydrolysis reaction of &#945;N<sup>+</sup> reported earlier for methionine and other sulfur-containing aminoacids and peptides, an intramolecular ring-closure reaction was found for <i>S</i>-alkylglutathiones.
ISSN:1420-3049

Similar Items