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Reactions of Aqueous Chlorine and Chlorine Dioxide with Tryptophan, N‐Methyltryptophan, and 3‐Indolelactic Acid: Kinetic and Mutagenicity Studies
Author(s) -
SEN A. C.,
OWUSUYAW J.,
WHEELER W. B.,
WEI C. I.
Publication year - 1989
Publication title -
journal of food science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.772
H-Index - 150
eISSN - 1750-3841
pISSN - 0022-1147
DOI - 10.1111/j.1365-2621.1989.tb07942.x
Subject(s) - chemistry , hypochlorous acid , tryptophan , chlorine dioxide , chlorine , aqueous solution , kinetics , inorganic chemistry , order of reaction , organic chemistry , amino acid , biochemistry , reaction rate constant , physics , quantum mechanics
Reactions of tryptophan, N‐methyltryptophan and 3‐indolelactic acid with aqueous chlorine or chlorine dioxide (ClO 2 ) in 0.1M potassium phosphate buffer, pH 6.0, were investigated to determine any structural relationships with regards to kinetics and mutagenicity. The reaction with ClO 2 followed pseudo‐first order kinetics, with the half‐life of the respective compounds being 36, 22, and 8 milliseconds. The formation of a dark precipitate in the reaction of tryptophan with HOCl precluded any kinetic comparison. The reaction products of tryptophan with hypochlorous acid (HOCl) or ClO 2 were mutagenic to Salmonella typhimurium TA98 and TA100; while those of N‐methyltryptophan with HOCl and ClO 2 were more mutagenic toward TA98. Higher recoveries of the reaction products were achieved by passing the acidified (pH 2.5) mixture through an XAD‐8/XAD‐2 resin column.