Intramolecular electron transfer between tyrosine and tryptophan photosensitized by a chiral pi,pi* aromatic ketone

Raquel E Galian; Lourdes Pastor-Pérez; Miguel A Miranda; Julia Pérez-Prieto

doi:10.1002/chem.200401118

Intramolecular electron transfer between tyrosine and tryptophan photosensitized by a chiral pi,pi* aromatic ketone

Chemistry. 2005 May 20;11(11):3443-8. doi: 10.1002/chem.200401118.

Authors

Raquel E Galian¹, Lourdes Pastor-Pérez, Miguel A Miranda, Julia Pérez-Prieto

Affiliation

¹ Departamento de Química Orgánica/ICMOL, Universidad de Valencia, Av. Vicent Andrés Estellés s/n, 46100 Burjassot, Valencia, Spain.

PMID: 15798972
DOI: 10.1002/chem.200401118

Abstract

The photochemical reaction of Trp and Tyr and related peptides with Suprofen (SUP) as sensitizer in H2O/CH3CN (28:1 v/v) solutions has been studied by time-resolved spectroscopy. The results show that SUP induces oxidation of both Trp and Tyr, as well as intramolecular-ET reactions in the related peptides. The influence of photosensitizer configuration on the involved processes has been studied by using the enantiomerically pure compounds. A significant chiral recognition is observed in which the concentration of the radicals formed after triplet quenching depends on the configuration of the chiral center; the quenching process is higher when using the (R)-SUP enantiomer.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Inflammatory Agents, Non-Steroidal / chemistry*
Kinetics
Models, Chemical
Photolysis
Stereoisomerism
Suprofen / chemistry*
Tryptophan / chemistry*
Tyrosine / chemistry*

Substances

Anti-Inflammatory Agents, Non-Steroidal
Tyrosine
Tryptophan
Suprofen