Enol-to-keto tautomerism of peptide groups

The Journal of Physical Chemistry. B
Katsumasa KamiyaAtsushi Oshiyama

Abstract

Density functional based simulations, performed on polyglycine containing an enol peptide group [-C(OH)N-] which is a structural isomer of a keto form [-CONH-], show that in the enol-to-keto tautomeric reaction, the enol peptide group is less stable than the keto form, and that the enol-to-keto tautomerism is characterized by a cis/trans isomerization of the C-N peptide bond. The rate-limiting step in the cis/trans isomerization is a hydrogen migration from O to N atoms in the peptide group with a transition state consisting of a four-membered ring in the cis configuration. An analysis of the cis/trans isomerization pathway shows that the mechanisms for the cis/trans isomerization are essentially different between the enol and keto forms.

References

Jul 5, 1990·Journal of Molecular Biology·D E StewartJ E Wampler
Feb 5, 1999·Journal of Molecular Biology·A JabsR Hilgenfeld
Dec 1, 1996·Physical Review. B, Condensed Matter·Y TateyamaS Tsuneyuki
Apr 15, 1990·Physical Review. B, Condensed Matter·D Vanderbilt
Apr 10, 1995·Physical Review Letters·Y MiyamotoS G Louie
Oct 28, 1996·Physical Review Letters·J P PerdewM Ernzerhof
Jan 4, 2001·Physical Review. E, Statistical Physics, Plasmas, Fluids, and Related Interdisciplinary Topics·A GabrielliL Pietronero
Jun 28, 2001·Journal of the American Chemical Society·C Schiene-Fischer, G Fischer
Jul 15, 2003·Physical Review Letters·Marcella IannuzziMichele Parrinello
Dec 16, 2003·Proceedings of the National Academy of Sciences of the United States of America·Tomitake TsukiharaShinya Yoshikawa
Jun 1, 2004·Physical Review Letters·Cristian MichelettiMichele Parrinello
Sep 17, 2004·Chemistry : a European Journal·Francesco Luigi GervasioMichele Parrinello
May 3, 2005·Proceedings of the National Academy of Sciences of the United States of America·Bernd Ensing, Michael L Klein

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Citations

Nov 18, 2011·The Journal of Organic Chemistry·Antonio RamirezSrinivas Tummala
Jan 10, 2012·The Journal of Physical Chemistry. a·Katsumasa KamiyaYasuteru Shigeta
May 14, 2011·Biochimica Et Biophysica Acta·Katsumasa Kamiya, Yasuteru Shigeta
Aug 17, 2016·Chemistry : a European Journal·Shrikant ThakareAnthony Harriman
Jun 23, 2020·Free Radical Research·Aiswarya PurushothamanDeepa Janardanan
Feb 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Till StensitzkiKarsten Heyne
Dec 7, 2010·Physical Chemistry Chemical Physics : PCCP·Roberto ScipioniTakahisa Ohno
Dec 13, 2012·Chemistry : a European Journal·Yun HuangGunter Fischer
Sep 12, 2007·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Katsumasa KamiyaAtsushi Oshiyama
Feb 13, 2021·Journal of the American Society for Mass Spectrometry·Simon DörnerSadia Bari
Jun 12, 2008·The Journal of Physical Chemistry. B·Simon MathieuGeorges Trinquier
Jul 20, 2007·Journal of the American Chemical Society·Katsumasa KamiyaAtsushi Oshiyama

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