Chemiluminescence associated with amino acid oxidation mediated by hypochlorous acid.
Although most amino acids readily react with hypochlorous acid (HOCl), only the reaction involving tryptophan (Trp) produces a measurable chemiluminescence (CL). Most of this luminescence takes place after total consumption of HOCI when the process is carried out in an excess of Trp. The quantum yield of the process is relatively low (2 x 10(-8) Einstein/mol HOCl reacted). The luminescence is attributed to free radical-mediated secondary reactions of the initially produced chloramines. This is supported by experiments showing that the chloramines produced when HOCl reacts with alanine are able to induce Trp chemiluminescence, and that this luminescence is partially quenched by free radical scavengers. The spectral changes and the effect of pH upon the observed luminescence are compatible with light emission from products produced in the free radical oxidation of Trp.
Aspée
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Departmento de Ciencias Químicas, Facultad de Química y Biologia, Universidad de Santiago de Chile.
Lissi
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D000596:Amino Acids / Q000737:chemistry*; D002082:Butylamines / Q000737:chemistry; D002700:Chloramines / Q000737:chemistry; D005453:Fluorescence; D005609:Free Radicals / Q000037:antagonists & inhibitors; D006863:Hydrogen-Ion Concentration; D006997:Hypochlorous Acid / Q000737:chemistry*; D007700:Kinetics; D008163:Luminescent Measurements; D010084:Oxidation-Reduction; D012862:Skatole / Q000737:chemistry; D013054:Spectrophotometry, Atomic; D013056:Spectrophotometry, Ultraviolet; D013057:Spectrum Analysis
D000596:Amino Acids; D002082:Butylamines; D002700:Chloramines; D005609:Free Radicals; D006997:Hypochlorous Acid; D012862:Skatole; C030816:chloramine; C032462:n-butylamine