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Kinetics and Mechanism of Oxidative Conversion of Methionine to Sulfone by Chloramine-B in Acid Medium

[ Vol. 8 , Issue. 1 ]

Author(s):

Kishore Cholkar*, Sujatha Veeranki, Puttaswamy Puttaswamy, Sanjay Anand and Netkal M. Made Gowda   Pages 37 - 45 ( 9 )

Abstract:


Background: Methionine, Met, is one of the sulfur containing amino acids required in the human body by certain biochemical reactions. Since Met is not biosynthesized in humans, it needs to be supplied externally in diet. Met is highly susceptible to oxidation.

Objective: The oxidation of Met to its sulfone by CAB in aqueous perchloric acid medium at 323 K has been kinetically studied.

Method: Effect of varying ionic strength, solvent composition, dielectric constant has been determined. Effect of reduction product of Chloramine-B (CAB), benzenesulfonamide, on the reaction rate has also been investigated.

Conclusion: The experimental rate law obtained is: rate = k׀ [CAB] [H2O]. Activation parameters have been evaluated using Arrhenius and Eyring plots. A mechanism consistent with the observed kinetic data has been discussed. A rate law has been derived based on the mechanism.

Keywords:

Chloramine-B, kinetics, mechanism, methionine, oxidation, rate law, reduction, sulfone.

Affiliation:

CUSTOpharm Inc, 2325 Camino Vida Roble, Carlsbad, CA 92011, Department of Chemistry, Western Illinois University, One University Circle, Macomb, IL 61455, Department of Studies in Chemistry, Manasagangothri, University of Mysore, Mysore 570 006, Department of Post-Graduate Studies in Chemistry, Central College, Bangalore University, Bangalore-560 001, Department of Chemistry, Western Illinois University, One University Circle, Macomb, IL 61455

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