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MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number:

Enzymes and Genes:

Curvularia inaequalis: chloride peroxygenaseInferred from experiment: CPO

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the Enzyme Commission system.

Most BioCyc compounds have been protonated to a reference pH value of 7.3. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Enzyme Commission Primary Name: chloride peroxidase

Enzyme Commission Synonyms: chloroperoxidase, CPO, vanadium haloperoxidase

Taxonomic Range: Bacteria , Fungi

Standard Gibbs Free Energy (ΔrG in kcal/mol): -60.948753Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
Brings about the chlorination of a range of organic molecules, forming stable C-Cl bonds. Can also act on Br- and I-.

Enzymes of this type are either heme-thiolate proteins, or contain vanadate. A secreted enzyme produced by the ascomycetous fungus Caldariomyces (Leptoxyphium) fumago is an example of the heme-thiolate type. It catalyses the production of hypochlorous acid by transferring one oxygen atom from H2O2 to chloride, as described in the following reaction:

chloride + hydrogen peroxide + H+ = hypochlorous acid + H2O

At a separate site it catalyses the chlorination of activated aliphatic and aromatic substrates, via HClO and derived chlorine species, as described in the following reaction:

an organic molecule + hypochlorous acid = an organochlorine compound + H2O

Also oxidizes bromide and iodide. In the absence of halides, it shows peroxidase (e.g. phenol oxidation) and peroxygenase activities. The latter inserts oxygen from H2O2 into, for example, styrene (side chain epoxidation) and toluene (benzylic hydroxylation), however, these activities are less pronounced than its activity with halides. Has little activity with non-activated substrates such as aromatic rings, ethers or saturated alkanes. The chlorinating peroxidase produced by ascomycetous fungi (e.g. Curvularia inaequalis) is an example of a vanadium chloroperoxidase, and is related to bromide peroxidase (EC It contains vanadate and oxidizes chloride, bromide and iodide into hypohalous acids. In the absence of halides, it peroxygenates organic sulfides and oxidizes 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) but no phenols.

Citations: [Morris66, Hager75, Sundaramoorthy95, tenBrink98, tenBrink00, Murali06, Kuhnel06, Manoj08]

Gene-Reaction Schematic

Gene-Reaction Schematic

Unification Links: KEGG:R00052

Relationship Links: BRENDA:EC:, ENZYME:EC:, IUBMB-ExplorEnz:EC:, UniProt:RELATED-TO:P04963, UniProt:RELATED-TO:P49053, UniProt:RELATED-TO:P49323, UniProt:RELATED-TO:Q53540

Revised 09-Feb-2011 by Caspi R, SRI International


Hager75: Hager LP, Hollenberg PF, Rand-Meir T, Chiang R, Doubek D (1975). "Chemistry of peroxidase intermediates." Ann N Y Acad Sci 244;80-93. PMID: 1056179

Kuhnel06: Kuhnel K, Blankenfeldt W, Terner J, Schlichting I (2006). "Crystal structures of chloroperoxidase with its bound substrates and complexed with formate, acetate, and nitrate." J Biol Chem 281(33);23990-8. PMID: 16790441

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Manoj08: Manoj KM, Hager LP (2008). "Chloroperoxidase, a janus enzyme." Biochemistry 47(9);2997-3003. PMID: 18220360

Morris66: Morris DR, Hager LP (1966). "Chloroperoxidase. I. Isolation and properties of the crystalline glycoprotein." J Biol Chem 241(8);1763-8. PMID: 5949836

Murali06: Murali Manoj K (2006). "Chlorinations catalyzed by chloroperoxidase occur via diffusible intermediate(s) and the reaction components play multiple roles in the overall process." Biochim Biophys Acta 1764(8);1325-39. PMID: 16870515

Sundaramoorthy95: Sundaramoorthy M, Terner J, Poulos TL (1995). "The crystal structure of chloroperoxidase: a heme peroxidase--cytochrome P450 functional hybrid." Structure 3(12);1367-77. PMID: 8747463

tenBrink00: ten Brink HB, Dekker HL, Schoemaker HE, Wever R (2000). "Oxidation reactions catalyzed by vanadium chloroperoxidase from Curvularia inaequalis." J Inorg Biochem 80(1-2);91-8. PMID: 10885468

tenBrink98: ten Brink HB, Tuynman A, Dekker HL, Hemrika W, Izumi Y, Oshiro T, Schoemaker HE, Wever R (1998). "Enantioselective Sulfoxidation Catalyzed by Vanadium Haloperoxidases." Inorg Chem 37(26);6780-6784. PMID: 11670813

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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