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Reactions Of Aqueous Chlorine With Alanylphenylalanine In Model Solutions And In A Wastewater, Thomas C. Fox

Chemistry & Biochemistry Theses & Dissertations

Model solutions of the dipeptide alanylphenylalanine were chlorinated to four different chlorine-to-amino nitrogen (Cl₂/Ala-Phe) mole ratios and analyzed by high performance liquid chromatography. At mole ratios ≤ 1, N-chloroalanylphenylalanine was the only major product. As the Cl₂/Ala-Phe mole ratio was increased to ≥ 2, N,N-dichloroalanylphenylalanine was the only major product. In model solutions (pH 7.0) the dichlorinated dipeptide decomposed (t_1/2= 4.1 hr) to form a stable N-chloroketimine, which has a half-life of 125 hours. This N-chloroketimine then decomposed to form phenylalanine.

To follow these reactions in a wastewater, alanyl-p-[ …