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

Autor(en)

Martin Wilke, Christian Brand, Josefin Wilke, Michael Schmitt

Abstrakt

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.

Organisation(en)

Quantenoptik, Quantennanophysik und Quanteninformation

Externe Organisation(en)

Heinrich-Heine-Universität Düsseldorf

Journal

Physical Chemistry Chemical Physics

Band

18

Seiten

13538-13545

Anzahl der Seiten

8

ISSN

1463-9076

DOI

https://doi.org/10.1039/C6CP02130A

Publikationsdatum

2016

Peer-reviewed

Ja

ÖFOS 2012

104026 Spektroskopie, 104017 Physikalische Chemie

Schlagwörter

ASJC Scopus Sachgebiete

Allgemeine Physik und Astronomie, Physical and Theoretical Chemistry

Link zum Portal

https://ucrisportal.univie.ac.at/de/publications/ea5598e7-9052-45ad-b3ea-5a4bbfec58c4