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Amide neighbouring-group effects in peptides: phenylalanine as relay amino acid in long-distance electron transfer

  • Nathanael, Joses G. School of Chemistry, Bio21 Institute, The University of Melbourne, Victoria, Australia
  • Gamon, Luke F. School of Chemistry, Bio21 Institute, The University of Melbourne, Victoria, Australia
  • Cordes, Meike Department of Chemistry, University of Basel, Switzerland
  • Rablen, Paul R. Department of Chemistry and Biochemistry, Swarthmore College, USA
  • Bally, Thomas Department of Chemistry, University of Fribourg, Switzerland
  • Fromm, Katharina M. Department of Chemistry, University of Fribourg, Switzerland
  • Giese, Bernd Department of Chemistry, University of Fribourg, Switzerland
  • Wille, Uta School of Chemistry, Bio21 Institute, The University of Melbourne, Victoria, Australia
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    04.05.2018
Published in:
  • ChemBioChem. - 2018, vol. 19, no. 9, p. 922–926
English 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.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/306925
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