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Issue 12, 2015
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Importance of dipole moments and ambient polarity for the conformation of Xaa–Pro moieties – a combined experimental and theoretical study

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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.

Graphical abstract: Importance of dipole moments and ambient polarity for the conformation of Xaa–Pro moieties – a combined experimental and theoretical study

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Article information


Submitted
18 Jun 2015
Accepted
27 Jul 2015
First published
12 Aug 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 6725-6730
Article type
Edge Article

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

C. Siebler, B. Maryasin, M. Kuemin, R. S. Erdmann, C. Rigling, C. Grünenfelder, C. Ochsenfeld and H. Wennemers, Chem. Sci., 2015, 6, 6725
DOI: 10.1039/C5SC02211H

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