Physicochemical Profiling of α-Lipoic Acid and Related Compounds

Arash Mirzahosseini, András Szilvay, B. Noszál

Research output: Contribution to journalArticle

Abstract

Lipoic acid, the biomolecule of vital importance following glycolysis, shows diversity in its thiol/disulfide equilibria and also in its eight different protonation forms of the reduced molecule. In this paper, lipoic acid, lipoamide, and their dihydro derivatives were studied to quantify their solubility, acid–base, and lipophilicity properties at a submolecular level. The acid–base properties are characterized in terms of six macroscopic, 12 microscopic protonation constants, and three interactivity parameters. The species-specific basicities, the pH-dependent distribution of the microspecies, and lipophilicity parameters are interpreted by various intramolecular effects, and contribute to understanding the antioxidant, chelate-forming, and enzyme cofactor behavior of the molecules observed.

Original languageEnglish
Pages (from-to)861-869
Number of pages9
JournalChemistry and Biodiversity
DOIs
Publication statusPublished - Jul 1 2016

Keywords

  • Acid-base
  • Lipoic acid
  • Lipophilicity
  • Microspeciation
  • NMR-pH titration
  • Solubility

ASJC Scopus subject areas

  • Biochemistry
  • Chemistry(all)
  • Bioengineering
  • Molecular Biology
  • Molecular Medicine

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