Horseradish peroxidase-catalyzed oxidation of chlorophyll a with hydrogen peroxide: characterization of the products and mechanism of the reaction

Biochimica Et Biophysica Acta
Paavo H HynninenErkki Kolehmainen

Abstract

Horseradish peroxidase was verified to catalyze, without any phenol, the hydrogen peroxide oxidation of chlorophyll a (Chl a), solubilized with Triton X-100. The 13(2)(S) and 13(2)(R) diastereomers of 13(2)-hydroxyChl a were characterized as major oxidation products (ca. 60%) by TLC on sucrose, UV-vis, (1)H, and (13)C NMR spectra, as well as fast-atom bombardment MS. A minor amount of the 15(2)-methyl, 17(3)-phytyl ester of Mg-unstable chlorin was identified on the basis of its UV-vis spectrum and reactivity with diazomethane, which converted it to the 13(1),15(2)-dimethyl, 17(3)-phytyl ester of Mg-purpurin 7. The side products (ca. 10%) were suggested to include the 17(3)-phytyl ester of Mg-purpurin 18, which is known to form easily from the Mg-unstable chlorin. The side products also included two red components with UV-vis spectral features resembling those of pure Chl a enolate anion. Hence, the two red components were assigned to the enolate anions of Chl a and pheophytin a or, alternatively, two different complexes of the Chl a enolate ion with Triton X-100. All the above products characterized by us are included in our published free-radical allomerization mechanism of Chl a, i.e. oxidation by ground-state dioxygen. The H...Continue Reading

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Citations

Oct 11, 2017·Journal of Experimental Botany·Benke KuaiStefan Hörtensteiner
May 16, 2019·Analytical and Bioanalytical Chemistry·Xiaoqiang WangChao Wang
Apr 27, 2021·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Morvarid AghayanForogh Adhami
Feb 16, 2011·Journal of Agricultural and Food Chemistry·María RocaRaúl de la Rosa

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