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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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Publication details

The article was received on 18 Jun 2015, accepted on 27 Jul 2015 and first published on 12 Aug 2015


Article type: Edge Article
DOI: 10.1039/C5SC02211H
Citation: Chem. Sci., 2015,6, 6725-6730
  • Open access: Creative Commons BY license
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    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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