Date of Award

Summer 1996

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

Frank E. Scully, Jr.

Committee Member

Robert L. Ake

Committee Member

Charles E. Bell

Call Number for Print

Special Collections LD4331.C45 F69

Abstract

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 (t1/2= 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-[3H]-phenylalanine was synthesized. Chlorination products were identified using this radiotracer and their stabilities were measured in the wastewater. The chlorination products formed and their stabilities were comparable to those in the model solutions.

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DOI

10.25777/ygdq-ne49

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