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

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 frequen...

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Published inPhysical chemistry chemical physics : PCCP Vol. 19; no. 1; pp. 496 - 502
Main Authors Vigorito, Annalisa, Calabrese, Camilla, Paltanin, Ettore, Melandri, Sonia, Maris, Assimo
Format Journal Article
LanguageEnglish
Published England 2017
Subjects
Absorption
Electronics
Flexibility
Isomers
Pharmacology
Rotational spectra
Solvents
Surface chemistry
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Summary: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 S 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.
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ISSN:1463-9076
1463-9084
DOI:10.1039/c6cp05606g