Sodium 2-mercaptoethanesulfonate in reversible adduct formation and water solubilization.
Sodium 2-mercaptoethanesulfonate (MESNA, coenzyme M) forms 1:1 covalent adducts with highly pi-electron deficient heterocycles. The addition is caused by the thiol function, and the adducts become water soluble as sulfonates. 1H NMR spectroscopy has been used to obtain information about electronic and steric effects on the equilibria between 2-pyrimidinones and their 1:1 MESNA adducts. The adducts are potential prodrugs for biologically interesting 2-pyrimidinones.
Rise
F
F
Institute of Chemistry, University of Uppsala, Sweden.
Undheim
K
K
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D009682:Magnetic Resonance Spectroscopy; D015080:Mesna / Q000737:chemistry*; D008968:Molecular Conformation; D012995:Solubility; D014867:Water
D014867:Water; D015080:Mesna