Relative reactivity of amino acids with chlorine in mixtures

Chongzheng Na, Terese M. Olson

Research output: Contribution to journalArticlepeer-review

37 Scopus citations


The relative reactivity of chlorine with amino acids is an important determinant of the resulting chlorination products in systems where chlorine is the limiting reagent, for example, in the human gastrointestinal tract after consumption of chlorine-containing water, or during food preparation with chlorinated water. Since few direct determinations of the initial reactivity of chlorine with amino acids have been made, 17 amino acids were compared in this study using competitive kinetic principles. The experimental results showed that (1) most amino acids have similar initial reactivities at neutral pH; (2) amino acids with thiol groups such as methionine and cysteine are exceptionally reactive and produce sulfoxides; (3) amino acids without thiol groups primarily undergo monochlorination of the amino nitrogen; and (4) glycine and proline are the least reactive. Dichlorination was estimated to occur with approximately 26% of the amino acid groups when the total amino acid: chlorine concentrations were equal.

Original languageEnglish
Pages (from-to)3220-3225
Number of pages6
JournalEnvironmental Science and Technology
Issue number9
StatePublished - May 1 2007


Dive into the research topics of 'Relative reactivity of amino acids with chlorine in mixtures'. Together they form a unique fingerprint.

Cite this