Importance of dipole moments and ambient polarity for the conformation of Xaa-Pro moieties - a combined experimental and theoretical study

Chemical Science
Christiane SieblerHelma Wennemers

Abstract

NMR spectroscopic studies with a series of proline derivatives revealed that the polarity of the environment has a significant effect on the trans : cis isomer ratio of Xaa-Pro bonds. Computational studies showed that this effect is due to differences in the overall dipole moments of trans and cis conformers. Comparisons between the conformational properties of amide and ester derivatives revealed an intricate balance between polarity effects and n → π* interactions of adjacent carbonyl groups. The findings have important implications for protein folding and signaling as well as the performance of proline-based stereoselective catalysts.

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Citations

Jun 5, 2020·Organic & Biomolecular Chemistry·Lin-E GuoYun-Bao Jiang
Aug 9, 2020·Beilstein Journal of Organic Chemistry·Vladimir Kubyshkin
Jun 14, 2017·Journal of Peptide Science : an Official Publication of the European Peptide Society·Anna Kusakiewicz-DawidDawid Siodłak
Mar 28, 2018·Journal of Peptide Science : an Official Publication of the European Peptide Society·Vladimir Kubyshkin, Nediljko Budisa
Dec 14, 2017·Beilstein Journal of Organic Chemistry·Vladimir Kubyshkin, Nediljko Budisa
Apr 12, 2017·Chemistry : a European Journal·Jasmine EgliHelma Wennemers
May 3, 2018·Chemical Communications : Chem Comm·Gert-Jan HofmanBruno Linclau
Aug 3, 2017·Organic & Biomolecular Chemistry·Vladimir Kubyshkin, Nediljko Budisa
Jan 30, 2021·Chemistry : a European Journal·Rajarshi MondalZackaria Nairoukh
Apr 9, 2021·Journal of the American Chemical Society·Jasmine EgliHelma Wennemers
Jun 22, 2021·Journal of the American Chemical Society·Jesús M DonesRonald T Raines
Feb 20, 2019·The Journal of Organic Chemistry·Gert-Jan HofmanBruno Linclau
Jul 13, 2016·Organic Letters·Takuhei YamamotoRichard S Glass
Jul 14, 2016·Organic Letters·Robert W NewberryRonald T Raines
Nov 23, 2018·The Journal of Organic Chemistry·Lin-E GuoYun-Bao Jiang
Mar 29, 2019·Journal of the American Chemical Society·Jasmine EgliHelma Wennemers
Dec 8, 2015·The Journal of Physical Chemistry. B·Yu-Ju LinJia-Cherng Horng
Oct 19, 2017·Journal of the American Chemical Society·Tobias Schnitzer, Helma Wennemers
Nov 5, 2019·Organic Letters·Jasmine EgliHelma Wennemers
Dec 29, 2016·Journal of the American Chemical Society·Anthony J MetranoScott J Miller

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Methods Mentioned

BETA
protein folding
NMR

Software Mentioned

COSMO
Turbomole

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