Some chemical properties and biological role of thiazolidine compounds

Life Sci. 1998;63(14):1251-67. doi: 10.1016/s0024-3205(98)00387-7.

Abstract

In this study we have investigated some chemical properties and the biological role of thiazolidine compounds, obtained by condensation of aminothiols (L- or D-cysteine, cysteamine) with pyridoxal-5'-phosphate. These products have been tested in presence of rat liver extracts (supernatant and mitochondria); bacterial suspensions and enzymes (L- or D-aminoacid oxidase, xanthine oxidase) with interesting results which gives evidence to a biological role. Their formation in vivo may represent the regulation of intracellular levels of pyridoxal-5'-phosphate and aminothiols. Moreover, we have analysed the two diastereoisomers of the thiazolidine compounds derived from L-cysteine and D-cysteine: we have succeeded to distinguish by NMR analysis the cis and the trans forms, concluding that the interconversion of the free forms is extremely rapid at pH 7: thus, it may be relevant for the protein bound forms.

MeSH terms

  • Animals
  • Bacteria / metabolism
  • Cysteamine / metabolism*
  • Cysteine / metabolism*
  • Female
  • Magnetic Resonance Spectroscopy
  • Male
  • Pregnancy
  • Pyridoxal Phosphate / metabolism*
  • Rats
  • Rats, Wistar
  • Stereoisomerism

Substances

  • Cysteamine
  • Pyridoxal Phosphate
  • Cysteine