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Photochemical Tyrosine Oxidation with a Hydrogen-Bonded Proton Acceptor by Bidirectional Proton-Coupled Electron Transfer. | LitMetric

Photochemical Tyrosine Oxidation with a Hydrogen-Bonded Proton Acceptor by Bidirectional Proton-Coupled Electron Transfer.

Chem Sci

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139-4307; Tel: 61d53 5537.

Published: August 2012

AI Article Synopsis

Article Abstract

Amino acid radical generation and transport are fundamentally important to numerous essential biological processes to which small molecule models lend valuable mechanistic insights. Pyridyl-amino acid-methyl esters are appended to a rhenium(I) tricarbonyl 1,10-phenanthroline core to yield rhenium-amino acid complexes with tyrosine ([Re]-Y-OH) and phenylalanine ([Re]-F). The emission from the [Re] center is more significantly quenched for [Re]-Y-OH upon addition of base. Time-resolved studies establish that excited-state quenching occurs by a combination of static and dynamic mechanisms. The degree of quenching depends on the strength of the base, consistent with a proton-coupled electron transfer (PCET) quenching mechanism. Comparative studies of [Re]-Y-OH and [Re]-F enable a detailed mechanistic analysis of a bidirectional PCET process.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3594118PMC
http://dx.doi.org/10.1039/C2SC20113EDOI Listing

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