Date of Award

Summer 1996

Document Type


Degree Name

Master of Science (MS)


Chemistry & Biochemistry



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


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.


In Copyright. URI: This Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).



Included in

Chemistry Commons