Amide Neighbouring-Group Effects in Peptides: Phenylalanine as Relay Amino Acid in Long-Distance Electron Transfer
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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 tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
Harvard
APA
Vancouver
Author
Bibtex
}
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