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

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Standard

Amide Neighbouring-Group Effects in Peptides : Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer. / Nathanael, Joses G.; Gamon, Luke F.; Cordes, Meike; Rablen, Paul R.; Bally, Thomas; Fromm, Katharina M.; Giese, Bernd; Wille, Uta.

I: ChemBioChem, Bind 19, Nr. 9, 04.05.2018, s. 922-926.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Harvard

Nathanael, JG, Gamon, LF, Cordes, M, Rablen, PR, Bally, T, Fromm, KM, Giese, B & Wille, U 2018, 'Amide Neighbouring-Group Effects in Peptides: Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer', ChemBioChem, bind 19, nr. 9, s. 922-926. https://doi.org/10.1002/cbic.201800098

APA

Nathanael, J. G., Gamon, L. F., Cordes, M., Rablen, P. R., Bally, T., Fromm, K. M., ... Wille, U. (2018). Amide Neighbouring-Group Effects in Peptides: Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer. ChemBioChem, 19(9), 922-926. https://doi.org/10.1002/cbic.201800098

Vancouver

Nathanael JG, Gamon LF, Cordes M, Rablen PR, Bally T, Fromm KM o.a. Amide Neighbouring-Group Effects in Peptides: Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer. ChemBioChem. 2018 maj 4;19(9):922-926. https://doi.org/10.1002/cbic.201800098

Author

Nathanael, Joses G. ; Gamon, Luke F. ; Cordes, Meike ; Rablen, Paul R. ; Bally, Thomas ; Fromm, Katharina M. ; Giese, Bernd ; Wille, Uta. / Amide Neighbouring-Group Effects in Peptides : Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer. I: ChemBioChem. 2018 ; Bind 19, Nr. 9. s. 922-926.

Bibtex

@article{c5c8bd68b98c4dfd8eeaf2140ce69f1a,
title = "Amide Neighbouring-Group Effects in Peptides: Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer",
abstract = "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.",
keywords = "density functional calculations, electron transfer, kinetics, neighboring-group effects, peptides, radical cations",
author = "Nathanael, {Joses G.} and Gamon, {Luke F.} and Meike Cordes and Rablen, {Paul R.} and Thomas Bally and Fromm, {Katharina M.} and Bernd Giese and Uta Wille",
year = "2018",
month = "5",
day = "4",
doi = "10.1002/cbic.201800098",
language = "English",
volume = "19",
pages = "922--926",
journal = "ChemBioChem",
issn = "1439-4227",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "9",

}

RIS

TY - JOUR

T1 - Amide Neighbouring-Group Effects in Peptides

T2 - Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer

AU - Nathanael, Joses G.

AU - Gamon, Luke F.

AU - Cordes, Meike

AU - Rablen, Paul R.

AU - Bally, Thomas

AU - Fromm, Katharina M.

AU - Giese, Bernd

AU - Wille, Uta

PY - 2018/5/4

Y1 - 2018/5/4

N2 - 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.

AB - 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.

KW - density functional calculations

KW - electron transfer

KW - kinetics

KW - neighboring-group effects

KW - peptides

KW - radical cations

UR - http://www.scopus.com/inward/record.url?scp=85045341917&partnerID=8YFLogxK

U2 - 10.1002/cbic.201800098

DO - 10.1002/cbic.201800098

M3 - Journal article

C2 - 29460322

AN - SCOPUS:85045341917

VL - 19

SP - 922

EP - 926

JO - ChemBioChem

JF - ChemBioChem

SN - 1439-4227

IS - 9

ER -

ID: 229275542