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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