Quantitative determination of SH groups using 19F NMR spectroscopy and disulfide of 2,3,5,6-tetrafluoro-4-mercaptobenzoic acid

Magn Reson Chem. 2005 Nov;43(11):902-9. doi: 10.1002/mrc.1652.

Abstract

A new method of measurement of thiol concentration by 19F NMR spectroscopy is developed. The method is based on the detection of products of the exchange reaction of thiols with a newly synthesized fluorinated disulfide, 2,3,5,6-tetrafluoro-4-mercaptobenzoic acid (BSSB). A significant broadening of the 19F NMR signal of BSSB in the presence of thiols was observed and attributed to the exchange reaction between the parent disulfide and 2,3,5,6-tetrafluoro-4-mercaptobenzoic acid. The rate constant for this reaction was found to be equal to (63 +/- 11) x 10(3) M(-1) s(-1) at pH 7.0. The method was applied for the measurement of concentration of glutathione and albumin in rat blood.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Benzoates / chemistry*
  • Disulfides / blood
  • Disulfides / chemistry*
  • Fluorine
  • Magnetic Resonance Spectroscopy / methods*
  • Magnetic Resonance Spectroscopy / standards
  • Male
  • Molecular Structure
  • Rats
  • Rats, Wistar
  • Reference Standards
  • Sulfhydryl Compounds / blood
  • Sulfhydryl Compounds / chemistry*

Substances

  • 2,3,5,6-tetrafluoro-4-mercaptobenzoic acid disulfide
  • 2,3,5,6-tetrafluoro-4-sulfanylbenzoic acid
  • Benzoates
  • Disulfides
  • Sulfhydryl Compounds
  • Fluorine