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Theoretical study of interactions between cysteine and perfluoropropanoic acid in gas and aqueous phase
Author(s) -
Holmes Tiffani M.,
Doskocz Jacek,
Wright Terrance,
Hill Glake A.
Publication year - 2008
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21892
Subject(s) - chemistry , hydrogen bond , cysteine , perfluorooctanoic acid , sulfur , amino acid , interaction energy , density functional theory , hydrogen , aqueous solution , hydrophobic effect , organic chemistry , computational chemistry , molecule , biochemistry , enzyme
The interaction of perfluoropropanoic acid (PFPA) with the amino acid cysteine was investigated using density functional theory. Previous studies suggest that the peroxisome proliferator chemical, perfluorooctanoic acid, is circulated throughout the body by way of sulfur‐containing amino acids. We present conformational analysis of the interactions of PFPA, a small model of perfluorooctanoic acid, with the sulfur‐containing amino acid which occur by the process of hydrogen bonding, in which the hydrogen of the sulfhydryl group interacts with the carboxyl oxygen, and the amino nitrogen forms a hydrogen bond with the hydrogen of the OH group of the fluorinated alkyl. We also show in our structures a recently characterized weak nonbonded interaction between divalent sulfur and a main chain carboxyl oxygen in proteins. B3LYP calculated free energies and interaction energies predict low‐energy, high‐interaction conformations for complex systems of perfluorinated fatty acid interactions with cysteine. © 2008 Wiley Periodicals, Inc. Int J Quantum Chem, 2009