Issue 1, 2017

Regarding the torsional flexibility of the dihydrolipoic acid's pharmacophore: 1,3-propanedithiol

Abstract

The conformational space of antioxidant dihydrolipoic acid has been explored through the investigation of its pharmacophore, 1,3-propanedithiol. Five of the possible 25 non-equivalent isomers (namely: gGGg′, gGGg, g′AGg, gAGg and g′AGg′) were observed in the 59.6–74.4 GHz frequency region using free-jet absorption rotational spectroscopy. Furthermore, for three of them, the 34S mono-substituted isotopologues were also detected in natural abundance. Theoretical simulations show that the balance of steric and electronic intramolecular interactions arises on a shallow conformational potential energy surface and suggest that in polar solvents the flexibility of the dithiol chain is greater than that in the isolated phase.

Graphical abstract: Regarding the torsional flexibility of the dihydrolipoic acid's pharmacophore: 1,3-propanedithiol

Supplementary files

Article information

Article type
Paper
Submitted
12 Aug 2016
Accepted
18 Nov 2016
First published
22 Nov 2016

Phys. Chem. Chem. Phys., 2017,19, 496-502

Regarding the torsional flexibility of the dihydrolipoic acid's pharmacophore: 1,3-propanedithiol

A. Vigorito, C. Calabrese, E. Paltanin, S. Melandri and A. Maris, Phys. Chem. Chem. Phys., 2017, 19, 496 DOI: 10.1039/C6CP05606G

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