KINETICS OF NITROSATION OF THIOPROLINE, THE PRECURSOR OF A MAJOR NITROSO COMPOUND IN HUMAN URINE, AND ITS ROLE AS A NITRITE SCAVENGER

Abstract

The kinetics of nitrosation of thioproline was studied. The rate of the reaction increased with decrease in pH, and was first-order with respect to nitrite concentration. The reaction rate was proportional to the concentration of total thioproline (free plus protonated), not to that of free thioproline. The initial reaction rate followed the equation:
rate=k₄×[thioproline]×[NaNO₂]×[H⁺]
The rate constant was found to be 49.4M^-2•sec^-1 at pH 2.0 and 37°. Thioproline acted as a nitrite scavenger, and suppressed the formation of a carcinogen, N-nitroso-N-benzylmethylamine, from N-benzylmethylamine and nitrite. More than 90% of the formation of N-nitroso-N-benzylmethylamine was inhibited by adding 20mM thioproline to a reaction mixture containing 20mM N-benzylmethylamine and 20mM sodium nitrite at pH 3.0 and 37°.