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Intramolecular Electron Transfer between Tyrosine and Tryptophan Photosensitized by a Chiral π,π* Aromatic Ketone
Author(s) -
Galian Raquel E.,
PastorPérez Lourdes,
Miranda Miguel A.,
PérezPrieto Julia
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200401118
Subject(s) - intramolecular force , chemistry , photochemistry , quenching (fluorescence) , tryptophan , photosensitizer , ketone , electron transfer , enantiomer , tyrosine , radical , stereochemistry , fluorescence , organic chemistry , amino acid , biochemistry , quantum mechanics , physics
Abstract The photochemical reaction of Trp and Tyr and related peptides with Suprofen (SUP) as sensitizer in H 2 O/CH 3 CN (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.