Issue 11, 2011
From the journal:

Photochemical & Photobiological Sciences

Mechanism of dioxindolylalanine formation by singlet molecular oxygen-mediated oxidation of tryptophan residues†‡

Graziella Eliza Ronsein,*a   Mauricio Cesar Bof de Oliveira,b   Marisa Helena Gennari de Medeirosa  and  Paolo Di Mascio*a  

* Corresponding authors

a Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil
E-mail: ronsein@iq.usp.br, pdmascio@iq.usp.br
Tel: +55 11 3091 8498

b Departamento de Polícia Federal, Ribeirão Preto, SP, Brazil

Abstract

The singlet molecular oxygen-oxidation of tryptophan generates diastereoisomeric dioxindolylalanine (diOia) along with hydroperoxides, alcohols and carbonyl compounds. Mechanistic investigations based on isotopic labeling and MS/MS analyses support diOia formation through a dioxetane intermediate.

Graphical abstract: Mechanism of dioxindolylalanine formation by singlet molecular oxygen-mediated oxidation of tryptophan residues

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Article information

DOI
https://doi.org/10.1039/C1PP05181D
Article type
Communication
Submitted
15 Jun 2011
Accepted
17 Aug 2011
First published
13 Sep 2011

Photochem. Photobiol. Sci., 2011,10, 1727-1730

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Mechanism of dioxindolylalanine formation by singlet molecular oxygen-mediated oxidation of tryptophan residues

G. E. Ronsein, M. C. B. de Oliveira, M. H. G. de Medeiros and P. Di Mascio, Photochem. Photobiol. Sci., 2011, 10, 1727 DOI: 10.1039/C1PP05181D

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