Issue 19, 2016

The conformational space of the neurotransmitter serotonin: how the rotation of a hydroxyl group changes all

Abstract

The 5-hydroxytryptamine receptors (5HTn) are optimized for 5-hydrotryptamine molecules, resulting in a significantly enhanced psychoactive response compared with the 4-, 6-, 7-isomers. This is despite their relatively similar energetic stabilities, excited state lifetimes and emission characteristics. In this work we investigate the conformational space of serotonin (5-hydroxytryptamine) using a combination of rotationally resolved electronic spectroscopy and ab initio calculations. The geometries of the four most abundant conformers are assigned from their molecular parameters in the electronic ground and excited state. We find a conformer-dependent competition between two polar groups trying to establish a hydrogen bond with the same H-atom in the most stable conformer of serotonin. The result explains some remarkable deviations with respect to the conformational space of the closely related neurotransmitter tryptamine. Based on the comparison to other 5-substituted indoles we propose to generalize this finding to explain the conformational preferences of indole-based neurotransmitters.

Graphical abstract: The conformational space of the neurotransmitter serotonin: how the rotation of a hydroxyl group changes all

Supplementary files

Article information

Article type
Paper
Submitted
31 Mar 2016
Accepted
19 Apr 2016
First published
26 Apr 2016
This article is Open Access
Creative Commons BY-NC license

Phys. Chem. Chem. Phys., 2016,18, 13538-13545

The conformational space of the neurotransmitter serotonin: how the rotation of a hydroxyl group changes all

M. Wilke, C. Brand, J. Wilke and M. Schmitt, Phys. Chem. Chem. Phys., 2016, 18, 13538 DOI: 10.1039/C6CP02130A

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