Cis-trans isomerization and puckering of proline residue

Biophysical Chemistry
Young Kee Kang, Ha Young Choi

Abstract

We report here the results on N-acetyl-L-proline-N'-methylamide (Ac-Pro-NHMe) calculated at the HF/6-31+G(d) level with the conductor-like polarizable continuum model (CPCM) of self-consistent reaction field methods to investigate the changes of backbone and prolyl ring along the cis-trans isomerization of the prolyl peptide bond. From the potential energy surface, the barrier to ring flip from the down-puckered conformation to the up-puckered one is estimated to be 2.5 and 3.2 kcal/mol for trans and cis conformers of Ac-Pro-NHMe, respectively. In particular, the ring flip seems to be inaccessible in the intermediate regions between trans and cis conformations, because of higher barriers (approximately 13-19 kcal/mol) to rotation of the prolyl peptide bond. The torsion angles for backbone and prolyl ring vary largely around the transition states at omega' approximately 120 degrees and -70 degrees for the prolyl peptide bond. Three kinds of puckering amplitudes show the same trend of puckering along the cis-trans isomerization although their absolute values are different. In particular, trans and cis conformations have the almost same degree of puckering. The cis populations and barriers to rotation of the prolyl peptide bond fo...Continue Reading

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Citations

Oct 10, 2008·The Journal of Physical Chemistry. B·Alejandra Flores-OrtegaCarlos Alemán
Nov 20, 2009·Proceedings of the National Academy of Sciences of the United States of America·Mahmoud MoradiCeleste Sagui
Oct 5, 2010·The Journal of Chemical Physics·Mahmoud MoradiCeleste Sagui
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Aug 3, 2017·Organic & Biomolecular Chemistry·Vladimir Kubyshkin, Nediljko Budisa
Jun 3, 2006·Proteins·Serena DonniniAndré H Juffer
Nov 7, 2008·Journal of Computational Chemistry·Young Kee Kang, Nam Sook Kang
Feb 4, 2009·Biopolymers·Young Kee KangByung Jin Byun
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Jun 27, 2019·Chemistry : a European Journal·Nicholas V CostantiniNeal J Zondlo
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Aug 19, 2007·The Journal of Physical Chemistry. B·Young Kee Kang
Oct 12, 2007·The Journal of Physical Chemistry. B·Young Kee Kang, Hae Sook Park
Jul 21, 2006·The Journal of Physical Chemistry. B·Il Keun Song, Young Kee Kang
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Dec 12, 2012·The Journal of Physical Chemistry. B·Robel B TeklebrhanFrank Schweizer
Feb 14, 2006·The Journal of Physical Chemistry. B·Il Keun Song, Young Kee Kang
Oct 20, 2006·The Journal of Physical Chemistry. B·Young Kee Kang
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