PMID: 43132Nov 1, 1979

Peroxide oxidation of indole to oxindole by chloroperoxidase catalysis

The Biochemical Journal
M D Corbett, B R Chipko


In the presence of chloroperoxidase, indole was oxidized by H2O2 to give oxindole as the major product. Under most conditions oxindole was the only product formed, and under optimal conditions the conversion was quantitative. This reaction displayed maximal activity at pH 4.6, although appreciable activity was observed throughout the entire pH range investigated, namely pH 2.5-6.0. Enzyme saturation by indole could not be demonstrated, up to the limit of indole solubility in the buffer. The oxidation kinetics were first-order with respect to indole up to 8 mM, which was the highest concentration of indole that could be investigated. On the other hand, 2-methylindole was not affected by H2O2 and chloroperoxidase, but was a strong inhibitor of indole oxidation. The isomer 1-methylindole was a poor substrate for chloroperoxidase oxidation, and a weak inhibitor of indole oxidation. These results suggest the possibility that chloroperoxidase oxidation of the carbon atom adjacent to the nitrogen atom in part results from hydrogen-bonding of the substrate N-H group to the enzyme active site.


Aug 15, 2012·Proceedings of the National Academy of Sciences of the United States of America·Hsin H Kuo, A Grant Mauk
Jun 21, 1983·Biochemistry·K RamakrishnanJ Fisher
Feb 11, 2003·The Journal of Biological Chemistry·Xianwen YiLowell P Hager
Dec 15, 1986·FEBS Letters·W WiesnerF Lingens

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