Publication: Conformational dependence of serotonin theoretical pK<inf>a</inf>prediction
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Issued Date
2006-03-21
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ISSN
00092614
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2-s2.0-33644686042
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Mahidol University
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SCOPUS
Bibliographic Citation
Chemical Physics Letters. Vol.420, No.4-6 (2006), 538-544
Suggested Citation
Jaturong Pratuangdejkul, Wichit Nosoongnoen, Georges Alexandre Guérin, Sylvan Loric, Marc Conti, Jean Marie Launay, Philippe Manivet Conformational dependence of serotonin theoretical pK<inf>a</inf>prediction. Chemical Physics Letters. Vol.420, No.4-6 (2006), 538-544. doi:10.1016/j.cplett.2006.01.035 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/23174
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Title
Conformational dependence of serotonin theoretical pK<inf>a</inf>prediction
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Abstract
In the present work we used quantum mechanics calculations to predict the two pKa's of 5-hydrotryptamine (5-HT). Proton dissociation reaction succeeded to predict the experimental pKa1corresponding to ionization of the protonated amine group but failed for pKa2corresponding to ionization of the 5-hydroxyl group. For pKa2, a cluster-continuum model including three water molecules in the first hydration shell around 5-hydroxyl and 5-hydroxide groups enabled us to reproduce the experimental pKa2value. Furthermore, we demonstrated that specific conformations of acid/base pair of 5-HT is critical to predict accurately the experimental pKa's of the flexible 5-HT molecule. © 2006 Elsevier B.V. All rights reserved.