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The Stereochemistry of the Chemical Expression of Darkness by József Csontos; Miklós Kálmán; Gyula Tasi is a Chemistry article available to read on EtoBox.

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Conformational analysis of melatonin (N-acetyl-5-methoxytryptamine) was performed at ab initio Hartree -Fock level: 128 conformers were obtained using 6-31G\* basis set. With the help of equivalence relations, the conformational hypersurface was divided into equivalence classes. It can be concluded that the side chains of melatonin are enantiotopic groups, i.e. melatonin has conformational planar docking chirality, and its conformers are correlated with each other as enantiomer, epimer, or diastereomer pairs. Based on these considerations, it is possible to explain the outcomes of restricted chiral melatonin analog experiments. It is suggested that conformers belonging to different equivalence classes should react with different receptor sites and elements of equivalent classes of 3re and 5si face side of the indole ring prefer the MT1, while 3si face side ones favor the MT2 melatonin receptor site.

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Author

József Csontos; Miklós Kálmán; Gyula Tasi

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0166-1280)

Published

2003

Language

EN

Field

Chemistry (Physical Sciences)