Issue 12, 2015

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
18 6 2015
Accepted
27 7 2015
First published
12 8 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 6725-6730

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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