Amide Neighbouring-Group Effects in Peptides: Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer

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Joses G. Nathanael, Luke F. Gamon, Meike Cordes, Paul R. Rablen, Thomas Bally, Katharina M. Fromm, Bernd Giese, Uta Wille

In nature, proteins serve as media for long-distance electron transfer (ET) to carry out redox reactions in distant compartments. This ET occurs either by a single-step superexchange or through a multi-step charge hopping process, which uses side chains of amino acids as stepping stones. In this study we demonstrate that Phe can act as a relay amino acid for long-distance electron hole transfer through peptides. The considerably increased susceptibility of the aromatic ring to oxidation is caused by the lone pairs of neighbouring amide carbonyl groups, which stabilise the Phe radical cation. This neighbouring-amide-group effect helps improve understanding of the mechanism of extracellular electron transfer through conductive protein filaments (pili) of anaerobic bacteria during mineral respiration.

OriginalsprogEngelsk
TidsskriftChemBioChem
Vol/bind19
Udgave nummer9
Sider (fra-til)922-926
Antal sider5
ISSN1439-4227
DOI
StatusUdgivet - 4 maj 2018

ID: 229275542