Chlorinations catalyzed by chloroperoxidase occur via diffusible intermediate(s) and the reaction components play multiple roles in the overall process

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1764, Issue 8, 2006, Pages 1325-1339

  Murali Manoj, Kelath ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Chlorination mechanism and kinetics; Chloroperoxidase; Haloperoxidase; Peroxidase

Indexed keywords

5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; AZIDE; CHLORIDE; CHLORIDE PEROXIDASE; PEROXIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHLORINATION; CONCENTRATION (PARAMETERS); DIFFUSION; ENZYME ACTIVE SITE; ENZYME SUBSTRATE; EPOXIDATION; PRIORITY JOURNAL; SOLUBILITY; SULFOXIDATION;

CATALYTIC DOMAIN; CHLORIDE PEROXIDASE; CHLORINE; EPOXY COMPOUNDS; FUNGI; INDENES; KINETICS; ONIUM COMPOUNDS; STYRENES; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 33747791727     PISSN: 15709639     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbapap.2006.05.012     Document Type: Article

References (87)

1. Shaw P.D., and Hager L.P. Chlorination. VI: chloroperoxidase: a component of the β-ketoadipate chlorinase system. J. Biol. Chem. 236 (1961) 1626-1630
2. Dawson J.H. Probing structure-function relations in heme-containing oxygenases and peroxidases. Science 240 (1988) 433-439
3. Ortiz de Montellano P. Structure, mechanism, and inhibition of cytochrome P450. Drug Metab. Dispos. 23 (1995) 1181-1187
4. Fann Y.-C., Gerber N.C., Omulski P.A., Hager L.P., Sligar S.G., and Hoffman B.M. ENDOR determination of heme ligation in chloroperoxidase and comparison with cytochrome P-450Cam. J. Am. Chem. Soc. 116 (1994) 5989-5990
5. Dunford B.H. Heme Peroxidases (1999), Wiley-VCH, NY 323-339
6. Green M.T., Dawson J.H., and Gray H.B. Oxoiron(IV) in chloroperoxidase compound II is basic: implications for P450 chemistry. Science 304 (2004) 1653-1656
7. Colonna S., Nagerro N., Manfredi A., Castella L., Gullotti M., Carrea G., and Pasta P. Enantioselective oxidations of sulfides catalyzed by chloroperoxidase. Biochemistry 29 (1990) 10465-10468
8. Fu H., Kondo H., Ichikawa Y., Look G.C., and Wong C.-H. Chloroperoxidase-catalyzed asymmetric synthesis: enantioselective reactions of chiral hydroperoxides with sulfides and bromohydration of glycols. J. Org. Chem. 57 (1992) 7265-7270
9. Allain E.J., Hager L.P., Deng L., and Jacobsen E.N. Highly enantioselective epoxidation of disubstituted alkenes with hydrogen peroxide catalyzed by chloroperoxidase. J. Am. Chem. Soc. 115 (1993) 4415-4416
10. Zaks A., and Dodds D.R. Chloroperoxidase-catalyzed asymmetric oxidations: substrate specificity and mechanistic study. J. Am. Chem. Soc. 117 (1995) 10419-10424
11. Lakner F.J., and Hager L.P. Enantioselective epoxidation of ω-bromo-2-methyl-1-alkenes catalyzed by chloroperoxidase: effect of chain length on selectivity and efficiency. J. Am. Chem. Soc. 119 (1996) 443-444
12. Kiljunen E., and Kanerva L.T. Novel applications of chloroperoxidase: enantioselective oxidation of racemic epoxyalcohols. Tetrahedron: Asymmetry 10 (1999) 3529-3535
13. Colonna S., Gagerro N., Richelmi C., and Pasta P. Recent biotechnological developments in the use of peroxidases. Trends Biotechnol. 17 (1999) 163-168
14. Murali Manoj K., and Hager L.P. The catalytic utility and versatility of chloroperoxidase. Rec. Res. Dev. Org. Chem. 6 (2002) 392-405
15. Water B., and Ballschmiter K. Biohalogenation as a source of halogenated ansioles in air. Chemosphere 22 (1991) 557-567
16. Carlsen L., and Larsen P. Enzymically mediated formation of chlorinated humic acids. Org. Geochem. 18 (1992) 477-480
17. Bello-Ramirez A.M., Carreon-Garabito B.Y., and Nava-Ocampo A.A. A theoretical approach to the mechanism of biological oxidation of organophosphorus pesticides. Toxicology 149 (2000) 63-68
18. Niedan V., Pavasars I., and Oberg G. Chloroperoxidase-mediated chlorination of aromatic groups in fulvic acid. Chemosphere 41 (2000) 779-785
19. Ortiz-Bermudez P., Srebotnik E., and Hammel K.E. Chlorination and cleavage of lignin structures by fungal chloroperoxidases. Appl. Environ. Microbiol. 69 (2003) 5015-5018
20. Reina R.G., Leri A.C., and Myneni S.C.B. Cl K-edge X-ray spectroscopic investigation of enzymatic formation of organochlorines in weathering plant material. Environ. Sci. Technol. 38 (2004) 783-789
21. Casey W.H. The fate of chlorine in soils. Science 295 (2002) 985-986
22. Hager L.P., Morris D.R., Brown F.S., and Eberwein H. Chloroperoxidase II: utilization of halogen ions. J. Biol. Chem. 241 (1966) 1769-1776
23. Blanke S.R., Martinis S.A., Sligar S.G., Hager L.P., Rux J.J., and Dawson J.H. Probing the heme coordination structure of alkaline chloroperoxidase. Biochemistry 35 (1996) 14537-14543
24. Hager L.P., Doubek D.L., Silverstein R.M., Harris J.H., and Martin J.C. Chloroperoxidase IX: structure of compound I. J. Am. Chem. Soc. 94 (1972) 4364-4366
25. Hollenberg P.F., Rand-Meir T., and Hager L.P. The reaction of chlorite with horseradish peroxidase and chloroperoxidase: enzymatic chlorination and spectral intermediates. J. Biol. Chem. 249 (1974) 5816-5825
26. Blanke S.R., and Hager L.P. Chemical modification of chloroperoxidase with diethylpyrocarbonate: evidence for the presence of an essential histidine residue. J. Biol. Chem. 265 (1990) 12454-12461
27. Neidleman S.L., Diassi P.A., Junta B., Palmore R.M., and Pan S.C. The enzymatic halogenation of steroids. Tetrahedron Lett. 7 (1966) 5337-5342
28. Neidleman S.L., and Levine S.D. Enzymatic bromohydrin formation. Tetrahedron Lett. 9 (1968) 4057-4059
29. Silverstein R.M., and Hager L.P. Chloroperoxidase XII: chloroperoxidase-catalyzed oxidation of thiols and disulfides to sulfenyl chlorides. Biochemistry 13 (1974) 5069-5073
30. Geigert J., Niedelman S.L., and Daleitos D.J. Novel haloperoxidase substrates: alkynes and cyclopropanes. J. Biol. Chem. 258 4 (1983) 2273-2277
31. Itoh N., Izumi Y., and Yamada H. Haloperoxidase-catalyzed halogenation of nitrogen-containing aromatic heterocycles represented by nucleic bases. Biochemistry 26 (1987) 282-289
32. Liu K.K.-C., and Wong C.-H. Enzymatic halohydration of glycols. J. Org. Chem. 57 (1992) 3748-3750
33. Libby R.D., Thomas J.A., Kaiser L.W., and Hager L.P. Chloroperoxidase halogenation reactions: chemical versus enzymic halogenation intermediates. J. Biol. Chem. 257 (1982) 5030-5037
34. Lambier A.M., and Dunford H.B. A steady state kinetic analysis of the reaction of chloroperoxidase with peracetic acid, chloride and 2-chlorodimedone. J. Biol. Chem. 258 (1983) 13558-13563
35. Ramakrishnan K., Oppenhuizen M.E., Saunders S., and Fisher J. Stereochemistry of peroxidase dependent halogenation. Biochemistry 22 (1983) 3271-3277
36. Dunford H.B., Lambier A.M., Kashem M.A., and Pickard M. On the mechanism of chlorination by chloroperoxidase. Arch. Biochem. Biophys. 252 (1987) 292-302
37. Libby R.D., Beachy T.M., and Phipps A.K. Quantitating direct chlorine transfer from enzyme to substrate in chloroperoxidase catalyzed reactions. J. Biol. Chem. 271 (1996) 21820-21827
38. Wagenknecht H.-A., and Woggon W.-D. Identification of intermediates in the catalytic cycle of chloroperoxidase. Chem. Biol. 4 (1997) 367-372
39. Wagenknecht H.-A., and Woggon W.-D. New active-site analogs of chloroperoxidase: syntheses and catalytic reactions. Angew. Chem. 36 (1997) 390-392
40. Wagenknecht H.-A., Claude C., and Woggon W.-D. New enzyme models of chloroperoxidase: improved stability and catalytic efficiency of iron porphyrinates containing a thiolato ligand. Helv. Chim. Acta 81 (1998) 1506-1520
41. Woggon W.-D., Wagenknecht H.-A., and Claude C. Synthetic active site analogues of heme-thiolate proteins: characterization and identification of intermediates of the catalytic cycles of cytochrome P450cam and chloroperoxidase. J. Inorg. Biochem. 83 (2001) 289-300
42. Woggon W.-D. Metalloporphyrines as active site analogues: lessons from enzymes and enzyme models. Acc. Chem. Res. 38 (2005) 127-136
43. Murphy C.D. New frontiers in biological halogenation. J. Appl. Microbiol. 94 (2003) 539-548
44. Griffin B.W. Mechanism of halide-stimulated activity of chloroperoxidase: evidence for enzymatic formation of free hypohalous acid. Biochem. Biophys. Res. Commun. 116 (1983) 873-879
45. Lee T.D., Geigert J., Daleitos D.J., and Hirano D.S. Neighboring group migration in enzyme mediated halohydrin formation. Biochem. Biophys. Res. Commun. 110 (1983) 880-883
46. Geigert J., Neidleman S.L., Dalietos D.J., and Dewitt S.K. Haloperoxidases: enzymic synthesis of α, β-halohydrins from gaseous alkanes. Appl. Environ. Microbiol. 45 (1983) 366-374
47. Griffin B.W., and Ashley P.L. Evidence for a radical mechanism of halogenation of monochlorodimedone catalyzed by chloroperoxidase. Arch. Biochem. Biophys. 233 (1984) 188-196
48. Griffin B.W., and Haddox R. Chlorination of NADH: similarities of the HOCl-supported and chloroperoxidase-catalyzed reactions. Arch. Biochem. Biophys. 239 (1985) 305-309
49. Neidleman S.L., and Geigert J. Biological halogenation: roles in nature, potential in industry. Endeavour 11 (1987) 5-15
50. Franssen M.C.R., and van der Plas H.C. The chlorination of barbituric acid and some of its derivatives by chloroperoxidase. Bioorg. Chem. 15 (1987) 59-70
51. G.H. Cady (1939), US Patent on Chlorine compounds 2,157,524, C.A. 33 6538.
52. Sundaramoorthy M., Terner J., and Poulos T.L. The crystal structure of chloroperoxidase: a heme peroxidase-cytochrome P450 functional hybrid. Structure 3 (1995) 1367-1377
53. Sundaramoorthy M., Terner J., and Poulos T.L. Stereochemistry of chloroperoxidase active site: crystallographic and molecular modelling studies. Chem. Biol. 5 (1998) 461-473
54. Murali Manoj K., Yi X., Rai G.P., and Hager L.P. A kinetic epoxidation assay for chloroperoxidase. Biochem. Biophys. Res. Commun. 266 (1999) 301-303
55. Margoliash E., Novogrodsky A., and Schejter A. Irreversible reaction of 3-amino-1, 2, 4-triazole and related inhibitors with the protein of catalase. Biochem. J. 74 (1960) 339-348
56. Holzwarth J.F., Meyer F., Pickard M., and Dunford H.B. Mechanism of azide binding to chloroperoxidase and horseradish peroxidase: use of an iodine laser temperature-jump apparatus. Biochemistry 27 (1988) 6628-6633
57. Atkins P.W. Physical Chemistry (1982), W.H. Freeeman and Co., San Fransisco 921-997
58. Hewson W.D., and Hager L.P. Mechanism of the chlorination reaction catalyzed by horseradish peroxidase with chlorite. J. Biol. Chem. 254 (1979) 3175-3181
59. Shahangian S., and Hager L.P. The reaction of chloroperoxidase with chlorite and chlorine dioxide. J. Biol. Chem. 256 (1981) 6034-6040
60. Voet D., and Voet J.G. Biochemistry (1990), John Wiley and Sons, Inc., New York 337
61. Murali Manoj K., and Hager L.P. Utilization of peroxide and its relevance in oxygen insertion reactions catalyzed by chloroperoxidase. Biochim. Biophys. Acta 1547 (2001) 408-417
62. Marquez L.A., and Dunford H.B. Chlorination of taurine by myeloperoxidase: kinetic evidence for an enzyme bound intermediate. J. Biol. Chem. 269 (1994) 7950-7956
63. Murali Manoj K., Lakner F.J., and Hager L.P. Epoxidation of indene by chloroperoxidase. J. Mol. Catal. B: Enzym. 9 (2000) 107-111
64. Kollonitsch J., Marburg S., and Perkins L.M. Enzymic formation of chiral structures in racemic form. J. Am. Chem. Soc. 92 (1970) 4489-4490
65. Watson W.D. Chlorination of phenol with chlorine and tert-butyl hypochlorite. J. Org. Chem. 39 (1974) 1160-1164
66. Neidleman S.L., and Geigert J. Biohalogenation (1986), Ellis Horwood Limited / John Wiley and Sons, Chichester
67. Gribble G.W. Naturally occurring organohalogen compounds-A comprehensive survey. Progress in the Chemistry of Organic Natural Products vol. 68 (1996), Springer-Verlag, New York
68. Lakner F.J., Cain K.P., and Hager L.P. Enantioselective epoxidation of ω-bromo-2-methyl-1-alkenes catalyzed by chloroperoxidase: effect of chain length on selectivity and efficiency. J. Am. Chem. Soc. 119 (1997) 443-444
69. Hager L.P., Lakner F.J., and Basavapathruni A. Chiral synthons via chloroperoxidase catalysis. J. Mol. Catal. B: Enzym. 5 (1998) 95-101
70. Brown F.S., and Hager L.P. Chloroperoxidase. IV: evidence for an ionic electrophilic substitution mechanism. J. Am. Chem. Soc. 89 (1967) 719-720
71. Shevelkova A.N., Salnikov Y.I., Kuzmina N.L., and Ryabov A.D. 'Thermodynamic' mechanism of catalysis by haloperoxidases. FEBS Lett. 383 (1996) 259-263
72. +. J. Am. Chem. Soc. 94 (1972) 3195-3200
73. Livingston R.S., and Bray W.C. Catalytic decomposition of hydrogen peroxide in an acid chlorine-chloride solution. J. Am. Chem. Soc. 47 (1925) 2069-2082
74. Livingston R.S., and Bray W.C. The catalytic decomposition of hydrogen peroxide in an acid chlorine-chloride solution. J. Am. Chem. Soc. 48 (1926) 405-406
75. Berliner E. The current state of positive halogenating agents. J. Chem. Educ. 43 (1966) 124-133
76. Connick R.E. The interaction of hydrogen peroxide and hypochlorous acid in acidic solutions containing chloride ion. J. Am. Chem. Soc. 69 (1947) 1509-1514
77. Fedorak P.M., Semple K.M., Vasquez-Duhalt R., and Westlake D.W.S. Chloroperoxidase mediated modifications of petroporphyrins and asphaltenes. Enzyme Microb. Technol. 15 (1993) 429-437
78. Mogollon L., Rodriguez R., Larrota W., Ortiz C., and Torres R. Biocatalytic removal of nickel and vanadium from petroporphyrins and asphaltenes. Appl. Biochem. Biotechnol. 70 (1998) 765-777
79. Vazquez-Duhalt R., Torres E., Valderrama B., and Le Borgne S. Will biochemical catalysts impact the petroleum refining industry?. Energy Fuels 16 (2002) 1239-1250
80. Franssen M.C.R. Haloperoxidases: useful catalysts for halogenation and oxidation reactions. Catal. Today 22 (1994) 441-457
81. Zaks A., Yabannavar A.V., Dodds D.R., Evans C.A., Das P.R., and Malchow R.A. A novel application of chloroperoxidase: preparation of gem halonitro Compounds. J. Org. Chem. 61 (1996) 8692-8695
82. Malmar I., and Sih C.J. Chloroperoxidase-catalyzed chlorination of didechloroaglucovancomycin and vancomycin. J. Mol. Catal. B: Enzym. 10 (2000) 545-549
83. Vazquez-Duhalt R., Ayala M., and Marquez-Rocha F.J. Biocatalytic chlorination of aromatic hydrocarbons by chloroperoxidase of Caldariomyces fumago. Phytochemistry 58 (2001) 929-933
84. Alvarez R.G., Hunter I.S., Suckling C.J., Thomas M., and Vitinius U. A novel transformation of benzofurans and related compounds catalyzed by a chloroperoxidase. Tetrahedron 57 (2001) 8581-8587
85. Grimvall A., and de Leer W.B. Naturally Produced Organohalogens (1995), Kluwer, Dordrecht
86. Myneni S.C. Formation of stable chlorinated hydrocarbons in weathering plant material. Science 295 (2002) 1039-1041
87. Murali Manoj K., and Hager L.P. A colorimetric method for the detection and quantification of chlorinating activity of hemeperoxidases. Anal. Biochem. 348 (2006) 84-86