A new structure of a serotonin salt: Comparison and conformational analysis of all known serotonin complexes

Denis Rychkov; Elena V. Boldyreva; Nikolay A. Tumanov

doi:10.1107/S0108270113019823

A new structure of a serotonin salt: Comparison and conformational analysis of all known serotonin complexes

Denis Rychkov, Elena V. Boldyreva, Nikolay A. Tumanov

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Abstract

Four serotonin salt structures (serotonin adipate, C₁₀H ₁₃N₂O⁺·C₆H₉O ₄ ^-, is a previously unknown structure) were analysed to understand the influence of the anion on serotonin conformation. Hydrogen bonding alone favours a flat conformation, whereas additional stacking interactions between ions may possibly account for the nonplanar conformation. Since molecular conformation, stability and biological activity are interrelated, one can consider influencing the chemical and biological properties of serotonin by selecting an appropriate counter-ion for salt formation.

Original language	English
Pages (from-to)	1055-1061
Number of pages	7
Journal	Acta crystallographica. Section C: Crystal structure communications
Volume	69
Issue number	9
DOIs	https://doi.org/10.1107/S0108270113019823
Publication status	Published - Sept 2013
Externally published	Yes

Keywords

conformation
crystal structure
Hirshfeld surfaces
hydrogen bonding
serotonin adipate
stacking interactions

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10.1107/S0108270113019823

Rychkov, Boldyreva, Tumanov - 2013 - A new structure of a serotonin salt comparison and conformational analysis of all known serotonin cFinal published version, 1.27 MB

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abstract = "Four serotonin salt structures (serotonin adipate, C10H 13N2O+·C6H9O 4 -, is a previously unknown structure) were analysed to understand the influence of the anion on serotonin conformation. Hydrogen bonding alone favours a flat conformation, whereas additional stacking interactions between ions may possibly account for the nonplanar conformation. Since molecular conformation, stability and biological activity are interrelated, one can consider influencing the chemical and biological properties of serotonin by selecting an appropriate counter-ion for salt formation.",

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AU - Tumanov, Nikolay A.

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AB - Four serotonin salt structures (serotonin adipate, C10H 13N2O+·C6H9O 4 -, is a previously unknown structure) were analysed to understand the influence of the anion on serotonin conformation. Hydrogen bonding alone favours a flat conformation, whereas additional stacking interactions between ions may possibly account for the nonplanar conformation. Since molecular conformation, stability and biological activity are interrelated, one can consider influencing the chemical and biological properties of serotonin by selecting an appropriate counter-ion for salt formation.

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KW - crystal structure

KW - Hirshfeld surfaces

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KW - stacking interactions

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JF - Acta crystallographica. Section C: Crystal structure communications

IS - 9

ER -

A new structure of a serotonin salt: Comparison and conformational analysis of all known serotonin complexes

Abstract

Keywords

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