Oxidation of Amino Acids, Peptides and Proteins by Ozone: A Review

REFERENCES

• Abdelmoez , W. , Nakahasi , T. and Yoshida , H . 2007 . Amino Acid Transformation and Decomposition in Saturated Subcritical Water Conditions . Ind. Eng. Chem. Res. , 46 : 5286 – 5294 .
   Web of Science ®Google Scholar
• Bader , H. and Hoigné , J . 1982 . Determination of Ozone in Water by the Indigo Method; A Submitted Standard Method . Ozone: Sci. Eng. , 4 : 169 – 176 .
   Web of Science ®Google Scholar
• Bailey , P.S. 1982 . “ Ozonation of Nucleophiles ” . In Ozonation in Organic Chemistry , Edited by: Wasserman , H.H. 155 – 201 . New York : Academic Press Inc .
   Google Scholar
• Banerjee , S.K. and Mudd , J.B. 1992 . Reaction of Ozone with Glycophorin in Solution and in Lipid Vesicles . Arch. Biochem. Phys. , 295 : 84 – 89 .
   PubMed Web of Science ®Google Scholar
• Berger , P. , Leitner , N.K.V. , Dore , M. and Legube , B. 1999 . Ozone and Hydroxyl Radicals Induced Oxidation of Glycine . Water Res. , 33 : 433 – 441 .
   Web of Science ®Google Scholar
• Berlett , B.S. , Levine , R.L. and Stadtman , E.R. 1996 . Comparison of the Effects of Ozone on the Modification of Amino Acid Residues in Glutamine Synthetase and Bovine Serum Albumin . J. Biol. Chem. , 271 : 4177 – 4182 .
   PubMed Web of Science ®Google Scholar
• Boreen , A.L. , Edhlund , B.L. , Cotner , J.B. and McNeill , K. 2008 . Indirect Photodegradation of Dissolved Free Amino Acids: The Contribution of Singlet Oxygen and the Differential Reactivity of DOM from Various Sources . Environ. Sci. Technol. , 42 : 5492 – 5498 .
   PubMed Web of Science ®Google Scholar
• Cataldo , F. 2003 . On the Action of Ozone on Proteins . Poly Deg Stab , 82 : 105 – 114 .
   Web of Science ®Google Scholar
• Cataldo , F. 2006 . Ozone Degradation of Biological Macromolecules: Proteins, Hemoglobin, RNA, and DNA . Ozone: Sci. Eng. , 28 : 317 – 328 .
   Web of Science ®Google Scholar
• Dooley , M.M. and Mudd , J.B. 1982 . Reaction of Ozone with Lysozyme under Different Exposure Conditions . Arch. Biochem. Phys. , 218 : 459 – 471 .
   PubMed Web of Science ®Google Scholar
• Duguet , J.P. , Anselme , C. and Mallevialle , J. 1988 . Identification of Organonitrogen Compounds in Waters and Their Changes in Systems for Potable Water Treatment . Water Supp. , 6 : 253 – 263 .
   Google Scholar
• Duguet , J.P. , Brodard , E. , Dussert , B. and Mallevialle , J. 1985 . Improvement in the Effectiveness of Ozonization of Drinking Water Through the Use of Hydrogen Peroxide . Ozone: Sci. Eng. , 7 ( 3 ) : 241 – 258 .
   Web of Science ®Google Scholar
• Enami , S. , Hoffmann , M.R. and Colussi , A.J. 2009 . Simultaneous Detection of Cysteine Sulfenate, Sulfinate, and Sulfonate During Cysteine Interfacial Ozonolysis . J. Phys. Chem. B , 113 : 9356 – 9358 .
   PubMed Web of Science ®Google Scholar
• Fimmen , R.L. , Trouts , T.D. , Richter , D.D. Jr. and Vasudevan , D. 2008 . Improved Speciation of Dissolved Organic Nitrogen in Natural Water: Amide Hydrolysis with Fluorescence Derivatization . J. Environ. Sci. , 20 : 1273 – 1280 .
   Web of Science ®Google Scholar
• Freeman , B.A. and Mudd , J.B. 1981 . Reaction of Ozone with Sulfhydryls of Human Erythrocytes . Arch. Biochem. Phys. , 208 : 212 – 220 .
   PubMed Web of Science ®Google Scholar
• Havel , H.A. 1996 . Spectroscopic Methods for Determining Protein Structure in Solution , New York : Wiley-VCH . pp. Chapter 2-Chapter 4.
   Google Scholar
• Higgins , M.J. , Adams , G. , Chen , Y. , Erdal , Z. , Forbes , R.H. Jr. , Glindermann , D. , Hargreaves , J.R. , McEwen , D. , Murthy , S.N. , Novak , J.T. and Witherspoon , J. 2008 . Role of Protein, Amino Acids, and Enzyme Activity on Odor Production from Anaerobically Digested and Dewatered Biosolids . Water Environ. Res. , 80 : 127 – 135 .
   PubMed Web of Science ®Google Scholar
• Hoigné , J. and Bader , H. 1983a . Rate Constants of Reactions of Ozone with Organic and Inorganic Compounds in Water—I: Non-dissociating Organic Compounds . Water Res. , 17 : 173 – 183 .
   Web of Science ®Google Scholar
• Hoigné , J. and Bader , H. 1983b . Rate Constants of Reactions of Ozone with Organic and Inorganic Compounds in Water—II: Dissociating Organic Compounds . Water Res. , 17 : 185 – 194 .
   Web of Science ®Google Scholar
• Hoigné , J. , Bader , H. , Haag , W.R. and Staehelin , J. 1985 . Rate Constants of Reactions of Ozone with Organic and Inorganic Compounds in Water—III: Inorganic Compounds and Radicals . Water Res. , 19 : 993 – 1004 .
   Web of Science ®Google Scholar
• Huang , J. , Graham , N , Templeton , M.R. , Zhang , Y. , Collins , C. and Nieuwenhuijsen , M. 2009 . A Comparison of the Role of Two Blue-Green Algae in THM and HAA Formation . Water Res. , 43 : 3009 – 3018 .
   PubMed Web of Science ®Google Scholar
• Ikehata , K. , Naghashkar , N.J. and El-Din , M.G. 2006 . Degradation of Aqueous Pharmaceuticals by Ozonation and Advanced Oxidation Processes: A Review . Ozone: Sci. Eng. , 28 ( 6 ) : 353 – 414 .
   Web of Science ®Google Scholar
• Karpel vel Leitner , N. , Delouane , B. , Legube , B. and Luck , F. 1999 . Effects of Catalysts during Ozonation of Salicylic Acid, Peptides and Humic Substances in Aqueous Solution . Ozone: Sci. Eng. , 21 : 261 – 276 .
   Web of Science ®Google Scholar
• Karpel vel Leitner , N. , Berger , P. and Legube , B. 2002 . Oxidation of Amino Groups by Hydroxyl Radicals in Relation to the Oxidation Degree of the Alpha-carbon . Environ. Sci. Technol. , 36 : 3083 – 3089 .
   PubMed Web of Science ®Google Scholar
• Knight , K.L. and Mudd , J.B. 1984 . The Reaction of Ozone with Glyceraldehyde-3-phosphate Dehydrogenase . Arch. Biochem. Biophys. , 229 ( 1 ) : 259 – 269 .
   PubMed Web of Science ®Google Scholar
• Kotiaho , T. , Eberlin , M.N. , Vainiotalo , P. and Kostiainen , R. 2000 . Electrospray Mass and Tandem Mass Spectrometry Identification of Ozone Oxidation Products of Amino Acids and Small Peptides . J. Amer. Soc. Mass Spectrom. , 11 : 526 – 535 .
   PubMed Web of Science ®Google Scholar
• Kuroda , M. , Sakiyama , F and Narita , K. 1975 . Oxidation of Tryptophan in Lysozyme by Ozone in Aqueous Solution . J. Biochem. , 78 : 641 – 651 .
   PubMed Web of Science ®Google Scholar
• Lagerwerf , F.M. , van de Weert , M. , Heerma , W. and Haverkamp , J. 1996 . Identification of Oxidized Methionine in Peptides . Rapid Commun. Mass Spectrom. , 10 : 1905 – 1910 .
   PubMed Web of Science ®Google Scholar
• Laplanche , A. and Martin , G. 1991 . “ Action de l'ozone sur les composes azotes moleculaires ” . In Ozone et Ozonation des eaux, coordinator , Edited by: Laviosier , E. W.J. Masschelein. Tec. et Doc.- Ed. Lavoisier .
   Google Scholar
• Le Lacheur , R.M. and Glaze , W.H. 1996 . Reactions of Ozone and Hydroxyl Radicals with Serine . Environ. Sci. Technol. , 30 : 1072 – 1080 .
   Web of Science ®Google Scholar
• Lee , W. and Westerhoff , P. 2009 . Formation of Organic Chloramines During Water Disinfection—Chlorination versus Chloramination . Water Res. , 43 : 2233 – 2239 .
   PubMed Web of Science ®Google Scholar
• Leh , F. , Warr , T.A. and Mudd , J.B. 1978 . Reaction of Ozone with Protease Inhibitors from Bovine Pancreas, Egg White, and Human Serum . Environ. Res. , 16 : 179 – 190 .
   PubMed Web of Science ®Google Scholar
• Lloyd , J.A. , Spraggins , J.M. and Johnston , M.V. 2006 . Peptide Ozonolysis: Product Structures and Relative Reactivities for Oxidation of Tyrosine and Histidine Residues . Am. Soc. Mass. Spec. , 17 : 1289 – 1298 .
   PubMed Web of Science ®Google Scholar
• Lytle , C.R. and Perdue , E.M. 1981 . Free, Proteinaceous, and Humic-Bound Amino Acids in River Water Containing High Concentrations of Aquatic Humus . Environ. Sci. Technol. , 15 : 224 – 228 .
   PubMed Web of Science ®Google Scholar
• Margerum , D.W. , Schurter , L.M. , Hobson , J. and Moore , E.E. 1994 . Water Chlorination Chemistry: Nonmetal Redox Kinetics of Chloramine and Nitrite Ion . Environ. Sci. Technol. , 28 : 331 – 337 .
   PubMed Web of Science ®Google Scholar
• Meiners , B.A. , Peters , R.E. and Mudd , J.B. 1977 . Effects of Ozone on Indole Compounds and Rat Lung Monoamine Oxidase . Environ. Res. , 14 : 99 – 112 .
   PubMed Web of Science ®Google Scholar
• Mudd , J.B. , Leavitt , R. , Ongun , A. and McManus , T.T. 1969 . Reaction of Ozone with Amino Acids and Proteins . Atmos. Environ. , 3 : 669 – 682 .
   PubMed Web of Science ®Google Scholar
• Mudd , J.B. , Dawson , P.J. , Tseng , S. and Liu , F. 1997 . Reaction of Ozone with Protein Tryptophans: Band III, Serum Albumin, and Cytochrome c . Arch. Biochem. Phys. , 338 : 143 – 149 .
   PubMed Web of Science ®Google Scholar
• Mumford , R.A. , Lipke , H. , Laufer , D.A. and Feder , W.A. 1972 . Ozone-induced Changes in Corn Pollen . Environ. Sci. Technol. , 6 ( 5 ) : 427 – 430 .
   Web of Science ®Google Scholar
• Na , C. and Olson , T.M. 2007 . Relative Reactivity of Amino Acids with Chlorine in Mixtures . Environ. Sci. Technol. , 41 : 3220 – 3225 .
   PubMed Web of Science ®Google Scholar
• Nebel , C. 1988 . Kirk-othmer Encyclopaedia of Chemical Technology , 3rd , 683 – 713 . New York : John Wiley & Sons .
   Google Scholar
• Niki , E. , Yamamoto , Y. , Saito , T. , Nagano , K. , Yokoi , S. and Kamiya , Y. 1983 . Ozonization of Organic Compounds. VII. Carboxylic Acids, Alcohols, and Carbonyl Compounds . J. Chem. Soc. Jpn. , 56 : 223 – 228 .
   Web of Science ®Google Scholar
• Pattison , D.I. and Davies , M.J. 2001 . Absolute Rate Constants for the Reaction of Hypochlorous Acid with Protein Side Chains and Peptide Bonds . Chem. Res. Toxicol. , 14 : 1453 – 1464 .
   PubMed Web of Science ®Google Scholar
• Pryor , W.A. , Giamalva , D.H. and Church , D.F. 1984 . Kinetics of Ozonation. 2. Amino Acids and Model Compounds in Water and Comparisons to Rates in Nonpolar Solvents . J. Am. Chem. Soc. , 106 : 7094 – 7100 .
   Web of Science ®Google Scholar
• Pryor , W.A. and Uppu , R.M. 1993 . A Kinetic Model for the Competitive Reactions of Ozone with Amino Acid Residues in Proteins in Reverse Micells . J. Biochem. , 265 : 3120 – 3126 .
   Google Scholar
• Rakovsky , S. and Zaikov , G.E. 1998 . Kinetics and Mechanism of Ozone Reactions with Organic and Polymeric Compounds in Liquid Phase , New York : Nova Science Publishers .
   Google Scholar
• Ramos , D.R. , Garcia , M.V. , Canle , M. , Santaballa , J.A. , Furtmuller , P.G. and Obinger , C. 2008 . Myeloperoxidase-Catalyzed Chlorination: The Quest for the Active Species . J. Inorg. Biochem. , 102 : 1300 – 1311 .
   PubMed Web of Science ®Google Scholar
• Sehested , K. , Corfitzen , H , Holcman , J. , Fischer , C.H. and Hart , E.J. 1991 . The Primary Reaction in the Decomposition of Ozone in Acidic Aqueous Solutions . J. Environ. Sci. Technol. , 25 : 1589 – 1596 .
   Web of Science ®Google Scholar
• Sehested , K. , Corfitzen , H. , Holcman , J. and Hart , E.J. 1998 . On the Mechanism of the Decomposition of Acidic O3 Solutions, Thermally or H2O2-initiated . J. Phys. Chem. A , 102 : 2667 – 2672 .
   Web of Science ®Google Scholar
• Shang , C. , Qi , Y. , Xie , L. , Liu , W. and Yang , X. 2005 . Kinetics of Cyanogen Chloride Destruction by Chemical Reduction Methods . Water Res. , 39 : 2114 – 2124 .
   PubMed Web of Science ®Google Scholar
• Simat , T.J. and Steinhart , H. 1998 . Oxidation of Free Tryptophan and Tryptophan Residues in Peptides and Proteins . J. Agric. Food Chem. , 46 : 490 – 498 .
   PubMed Web of Science ®Google Scholar
• Smith , C.E. , Stack , M.S. and Johnson , D.A. 1987 . Ozone Effects on Inhibitors of Human Neutrophil Proteinases . Arch. Biochem. Phys. , 253 : 146 – 155 .
   PubMed Web of Science ®Google Scholar
• Spanggord , R.J. and McClurg , V.J. 1978 . Ozone/Chlorine Dioxide Oxidation Products of Organic Materials , Edited by: Rice , R.G. and Contruvo , J.A. 115 – 123 . Cleveland, OH : Ozone Press International, 1978 .
   Google Scholar
• Staehelin , J. and Hoigné , J. 1982 . Decomposition of Ozone in Water: Rate of Initiation by Hydroxide Ions and Hydrogen Peroxide . Environ. Sci. Technol. , 16 : 676 – 681 .
   Web of Science ®Google Scholar
• Stelmaszynska , T. and Zgliczynski , J.M. 1978 . N-(2-oxoacyl)amino Acids and Nitriles as Final Products of Dipeptide Chlorination Mediated by the Myeloperoxidase/H2O2/Cl- System . Eur. J. Biochem. , 92 : 301 – 308 .
   PubMedGoogle Scholar
• Stewart , D.J. , Napolitano , M.J. , Bakhmutova-Albert , E.V. and Margerum , D.W. 2008 . Kinetics and Mechanisms of Chlorine Dioxide Oxidation of Tryptophan . Inorg. Chem. , 47 ( 5 ) : 1639 – 1647 .
   PubMed Web of Science ®Google Scholar
• Thurman , E.M. 1985 . Organic Geochemistry of Natural Waters , Edited by: Nijhoff , M. and Junk , W. The Netherlands : Dordrecht .
   Google Scholar
• Tomiyasu , H. , Fukutomi , H. and Gordon , G. 1985 . Kinetics and Mechanism of Ozone Decomposition in Basic Aqueous Solution . Inorg. Chem. , 24 : 2962 – 2966 .
   Web of Science ®Google Scholar
• Uppu , R.M. and Pryor , W.A. 1994 . The Reactions of Ozone with Proteins and Unsaturated Fatty Acids in Reverse Micelles . Chem. Res. Toxicol. , 7 : 47 – 55 .
   PubMed Web of Science ®Google Scholar
• Verweij , H. , Christianse , K. and Van Steveninck , J. 1982a . Different Pathways of Tyrosine Oxidation by Ozone . Chemosphere , 11 : 721 – 725 .
   Web of Science ®Google Scholar
• Verweij , H. , Christianse , K. and Van Steveninck , J. 1982b . Ozone-Induced Formation of o,o'-Dityrosine Cross-links in Proteins . Biochim. Biophys. Acta , 701 : 180 – 184 .
   PubMed Web of Science ®Google Scholar
• von Gunten , U. 2003 . Ozonation of Drinking Water: Part I. Oxidation Kinetics and Product Formation . Water Res. , 37 : 1443 – 1467 .
   PubMed Web of Science ®Google Scholar
• Yamamoto , Y. , Niki , E. and Kamiya , Y. 1982 . Ozonization of Organic Compounds. VI. Relative Reactivity of Protic Solvents Toward Carbonyl Oxide . J. Chem. Soc. Jpn. , 55 : 2677 – 2678 .
   Web of Science ®Google Scholar
• Yang , X. and Shang , C. 2004 . Chlorination Byproduct Formation in the Presence of Humic Acid, Model Nitrogenous Organic Compounds, Ammonia, and Bromide . Environ. Sci. Technol. , 38 : 4995 – 5001 .
   PubMed Web of Science ®Google Scholar