Kinetics and thermodynamics of oxidation mediated reaction in L-cysteine and its methyl and ethyl esters in dimethyl sulfoxide-d6 by NMR spectroscopy

Ryan J. Dougherty, Jaideep Singh, Viswanathan V Krishnan

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

L-Cysteine (L-Cys), L-Cysteine methyl ester (L-CysME) or L-Cysteine ethyl ester (L-CysEE), when dissolved in dimethyl sulfoxide, undergoes an oxidation process. This process is slow enough and leads to nuclear magnetic resonance (NMR) spectral changes that could be monitored in real time. The oxidation mediated transition is modeled as a pseudo-first order kinetics and the thermodynamic parameters are estimated using the Eyring's formulation. L-Cysteine and their esters are often used as biological models due to the remarkable thiol group that can be found in different oxidation states. This oxidation mediated transition is due to the combination of thiol oxidation to a disulfide followed by solvent-induced effects may be relevant in designing cysteine-based molecular models.

Original languageEnglish (US)
Pages (from-to)196-200
Number of pages5
JournalJournal of Molecular Structure
Volume1131
DOIs
StatePublished - Mar 5 2017

Keywords

  • C
  • H
  • Kinetics
  • L-cysteine. L-Cysteine methyl ester (L-CysME) and L-Cysteine ethyl ester (L-CysEE)
  • NMR
  • Oxidation
  • Short title
  • Solvent effect

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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