Conformational dependence of serotonin theoretical pKa prediction

Autor:	Jean-Marie Launay, Georges-Alexandre Guérin, Sylvan Loric, Jaturong Pratuangdejkul, Philippe Manivet, Wichit Nosoongnoen, Marc Conti
Rok vydání:	2006
Předmět:	Work (thermodynamics) Solvation shell Chemistry Computational chemistry Ionization Proton dissociation General Physics and Astronomy Molecule Amine gas treating Protonation Physical and Theoretical Chemistry
Zdroj:	Chemical Physics Letters. 420:538-544
ISSN:	0009-2614
DOI:	10.1016/j.cplett.2006.01.035
Popis:	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 pKa1 corresponding to ionization of the protonated amine group but failed for pKa2 corresponding 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 pKa2 value. 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a38680cc5ec786154df14817b9a31878 https://doi.org/10.1016/j.cplett.2006.01.035 Zobrazit plný text záznamu Full Text from ScienceDirect