Peroxidation of polyunsaturated fatty acid methyl esters catalyzed by N-methyl benzohydroxamic acid: A new and convenient method for selective synthesis of hydroperoxides and alcohols

Chemical Research in Toxicology

Volumn 18, Issue 2, 2005, Pages 349-356

  Punta, Carlo ^a   Rector, Christopher L ^b   Porter, Ned A ^b  

^a POLITECNICO DI MILANO   (Italy)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BENZOHYDROXAMIC ACID; ESTER DERIVATIVE; HYDROGEN; HYDROPEROXIDE DERIVATIVE; LINOLEATE ESTER DERIVATIVE; LINOLEIC ACID; LIPID; LIPID HYDROPEROXIDE; METHYL GROUP; N METHYLBENZOHYDROXAMIC ACID; POLYUNSATURATED FATTY ACID; RADICAL; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CATALYSIS; CATALYST; CHEMICAL REACTION; OXIDATION; PEROXIDATION; PHOTOLYSIS; PROTON TRANSPORT; REACTION ANALYSIS; RECYCLING; REPRODUCIBILITY; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

ALCOHOLS; CATALYSIS; ESTERS; FATTY ACIDS, UNSATURATED; HYDROXAMIC ACIDS; MOLECULAR STRUCTURE; PEROXIDES; TIME FACTORS;

EID: 13844269347     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049685x     Document Type: Article

References (32)

1. Hamberg, M., and Samuelsson, B. (1974) Prostaglandin endoperoxides. III. Novel transformations of arachidonic acid in human platelets. Proc. Natl. Acad. Sci. U.S.A. 71, 3400-3404.
2. Nugteren, D. H. (1975) Arachidonate lipoxygenase in blood platelets. Biochim. Biophys. Acta 380, 299-307.
3. Borgeat, P., and Samuelsson, B. (1979) Arachidonic acid metabolism in polymorphonuclear leukocytes. III. Effects of ionophore A23187. Proc. Natl. Acad. Sci. U.S.A. 76, 2148-2152.
4. Borgeat, P., and Samuelsson, B. (1979) Transformation of arachidonic acid by rabbit polymorphonuclear leukocytes. Formation of a novel dihydroxyeicosatetraenoic acid. J. Biol. Chem. 254, 2643-2646.
5. Marnett, L. J. (2000) Oxyradicals and DNA damage. Carcinogenesis 21, 361-370.
6. Sevarian, A., and Ursini, F. (2000) Lipid peroxidation in membranes and low-density lipoproteins: Similarities and differences. Free Radical Biol. Med. 29, 306-311.
7. Spiteller, G., Spiteller, D., Jiva, W., Kiessling, U., Dudda, A., Weisser, M., Hecht, S., and Schwarz, C. (2000) Age and age-dependent diseases, a consequence of lipid peroxidation? In Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer: Research Report (Waldemar, A., Ed.) pp 179-208, Wiley-VCH, Weinheim.
8. Steinberg, D., Parhsarathy, S., Carew, T. E., Khoo, J. C., and Witzlum, J. L. (1989) Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320, 915-924.
9. Chisolm, G. M., and Steinberg, D. (2000) The oxidative modification hypothesis of atherogenesis: An overview. Free Radical Biol. Med. 28, 1815-1826.
10. Porter, N. A., Logan, J., and Kontoyiannidou, V. (1979) Preparation and purification of arachidonic acid hydroperoxides of biological importance. J. Org. Chem. 44, 3177-3181.
11. Porter, N. A. (1986) Mechanisms for the autoxidation of polyunsaturated lipids. Acc. Chem. Res. 19, 262-268.
12. Hamberg, M., and Samuelsson, B. (1967) Specificity of the oxygenation of unsaturated fatty acids catalyzed by soybean lipoxidase. J. Biol. Chem. 242, 5329-5335.
13. Coates, R. M., and Firsan, S. J. (1986) Thioimidate N-oxides: nitrones of thioesters. J. Org. Chem. 26, 5198-5209.
14. +) ion spray-mass spectrometry of peroxidation products of cholesterol linoleate and cholesterol arachidonate: High performance liquid chromatography-mass spectrometry analysis of peroxide products from polyunsaturated lipid autoxidation. J. Am. Chem. Soc. 122, 8042-8055.
15. Seal, J. R., and Porter, N. A. (2004) Liquid chromatography coordination ion-spray mass spectrometry (LC-CIS-MS) of docosahexaenoate ester hydroperoxides. Anal. Bioanal. Chem. 378, 1007-1013.
16. Ishii, Y., Sakaguchi, S., and Iwahama, T. (2001) Innovation of hydrocarbon oxidation with molecular oxygen and related reactions. Adv. Synth. Catal. 343, 393-427.
17. Minisci, F., Recupero, F., Pedulli, G. F., and Lucarini, M. (2003) Transition metal salts catalysis in the aerobic oxidation of organic compounds. Thermochemical and kinetic aspects and new synthetic developments in the presence of N-hydroxy-derivative catalysts. J. Mol. Catal. A 204-205, 63-90.
18. Minisci, F., Recupero, F., Cecchetto, A., Gambarotti, C., Punta, C., Faletti, R., Paganelli, R., and Pedulli, G. F. (2004) Mechanisms of the aerobic oxidation of alcohols to aldehydes and ketones, catalysed under mild conditions by persistent and nonpersistent nitroxyl radicals and transition metal salts - polar, enthalpic, and captodative effects. Eur. J. Org. Chem. 109-119.
19. Amorati, R., Lucarini, M., Mugnaini, V., Pedulli, G. F., Minisci, F., Recupero, F., Fontana, F., Astolfi, P., and Greci, L. (2003) Hydroxylamines as oxidation catalysts: Thermochemical and kinetic studies. J. Org. Chem. 68, 1747-1754.
20. Howard, J. A., and Ingold, K. U. (1967) Absolute rate constants for hydrocarbon autoxidation. VI. Alkyl, aromatic, and olefinic hydrocarbons. Can. J. Chem. 45, 793-802.
21. Porter, N. A., Lehman, L. S., Weber, B. A., and Smith, K. J. (1981) Unified mechanism for polyunsaturated fatty acid autoxidation. Competition of peroxy radical hydrogen atom abstraction, β-scission, and cyclization. J. Am. Chem. Soc. 103, 6447-6455.
22. Mohoney, L. R., Mendenhall, G. D., and Ingold, K. U. (1973) Calometric and equilibrium studies on some stable nitroxide and iminoxy radicals. Approximate oxygen-hydrogen bond dissociation energies in hydroxylamines and oximes. J. Am. Chem. Soc. 95, 8610.
23. Coseri, S., and Ingold, K. U. (2004) Distinguishing between abstraction and addition as the first step in the reaction of nitroxyl radicals with cyclohexene. Org. Lett. 6, 1641-1643.
24. Pratt, D. A., Mills, J. H., and Porter, N. A. (2003) Theoretical calculations of carbon-oxygen bond dissociation enthalphies of peroxyl radicals formed in the autoxidation of lipids. J. Am. Chem. Soc. 125, 5801-5810.
25. Chan, H. W.-S., and Levett, G. (1977) Autoxidation of methyl linolenate: Analysis of methyl hydroxylinolenate isomers by high performance liquid chromatography. Lipids 12, 837-840.
26. Funk, M. O., Isaac, R., and Porter, N. A. (1976) Preparation and purification of lipid hydroperoxides from arachidonic and gamma linolenic acids. Lipids 11, 113-117.
27. Feussner, I., and Kühn, H. (2000) Application of lipoxygenases and related enzymes for the preparation of oxygenation lipids. In Enzymes in Lipid Modification (Bornscheuer, U. T., Ed.) pp 309-336, Wiley-VCH, Weinheim.
28. VanRollins, M., and Murphy, R. C. (1984) Autoxidation of docosahexaenoic acid: Analysis of 10 isomers of hydroxydocosahexaenoate. J. Lipid Res. 25, 507-517.
29. Neff, W. E., Frankel, E. N., and Weisleder, D. (1982) Photosensitized oxidation of methyl linolenate. Secondary products. Lipids 17, 780-790.
30. Bild, G. S., Ramadoss, C. S., Lim, S., and Axelrod, B. (1977) Double dioxygenation of arachidonic acid by soybean lipoxygenase-1. Biochem. Biophys. Res. Commun. 74, 949-954.
31. Neff, W. E., Frankel, E. N., and Weisleder, D. (1981) High-pressure liquid chromatography of autoxidized lipids. II. Hydroperoxy-cyclic peroxides and other secondary products from methyl linoleate. Lipids 16, 439-448.
32. Coxon, D. T., Peers, K. E., and Rigby, N. M. (1984) Selective formation of dihydroperoxides in the α-tocopherol inhibited autoxidation of methyl linoleate. J. Chem. Soc. Chem. Commun. 67-68.