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 in | Physical chemistry chemical physics : PCCP Vol. 19; no. 1; pp. 496 - 502 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
England
2017
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Subjects | |
Online Access | Get full text |
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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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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1463-9076 1463-9084 |
DOI: | 10.1039/c6cp05606g |