Oxidation of Amino Acids, Peptides, and Proteins

Virender K. Sharma is Professor of Chemistry as well as Director of the Center of Ferrate Excellence at Florida Institute of Technology. Dr. Sharma has organized several symposia, including “Nanotechnology and the Environment: Green Technology” at the 243rd American Chemical Society National Meeting in 2012. He is also coauthor of Mossbauer Spectroscopy: Application in Chemistry, Biology, Industry and Nanotechnology (Wiley).

• PREFACE TO SERIES xiiiINTRODUCTION xv1 Reactive Species 11.1 Diseases 31.1.1 Neurodegenerative Diseases 31.1.1.1 Alzheimers Disease 51.1.1.2 Parkinson’s Disease 51.1.2 Metals in Human Diseases 61.2 Protein Structure 91.2.1 Oxidative Labeling 101.2.1.1 Carbonyl Labeling 101.2.1.2 Cysteine Residue Labeling 101.2.1.3 Reactive Species Labeling 101.2.1.4 Hydroxyl Radical Labeling 121.2.2 Other Techniques 131.3 Reactive Species 201.3.1 Halogen Species 201.3.2 Oxygen Species 211.3.3 Nitrogen Species 221.3.4 Sulfur Species 221.3.5 High-Valent Cr, Mn, and Fe Species 251.4 Reactive Species in Environmental Processes 261.4.1 Atmospheric Environment 261.4.2 Disinfection By-Products (DBP) 271.4.3 Oxidation Processes for Purifying Water 29References 302 Acid–Base Properties 522.1 Dissociation Constants 542.2 Speciation 622.2.1 Protonation 622.2.2 Metal Complexes 632.2.2.1 Iron 642.2.2.2 Copper, Zinc, and Nickel 66References 693 Halogenated Species 783.1 Hypohalogens 793.1.1 Hypochlorite 793.1.1.1 Kinetics of HOCl 793.1.1.2 Products of HOCl Oxidation 833.1.2 Hypobromite 883.1.2.1 Kinetics of HOBr 883.1.2.2 Products of HOBr Oxidation 893.1.3 Hypothiocyanous 903.1.3.1 Kinetics of HOSCN 913.1.3.2 Products of HOSCN Oxidation 923.2 Halamines 933.2.1 Hydrolysis of Halamines 933.2.2 Halogen Transfer by Halamines 943.2.3 Reduction of Halamines 963.3 Chlorine Dioxide 963.3.1 Generation of ClO2 1013.3.2 Decomposition of ClO2 1013.3.3 Reactivity of ClO2 1043.3.3.1 Amino Acids, Peptides, and Proteins 1043.4 Conclusions 109References 1104 Reactive Oxygen Species 1224.1 Superoxide 1224.1.1 Generation 1224.1.2 Properties 1234.1.3 Reactivity 1254.1.4 Metalloenzymes 1294.1.4.1 Manganese Superoxide Dismutase 1314.1.4.2 Iron Superoxide Dismutase 1344.1.4.3 Iron Superoxide Reductase (FeSOR) 1354.2 Singlet Oxygen 1404.2.1 Reactivity 1424.3 Ozone 1534.3.1 Reactivity 1544.4 Hydroxyl Radical 1624.4.1 Generation 1624.4.2 Reactivity 1644.4.2.1 Main-Chain Cleavage of Protein 1654.4.2.2 Oxidation of Amino Acid Side Chains 169Aliphatic Side Chains 169Sulfur-Containing Side Chains 172Acidic Side Chains 175Basic Side Chains 175Aromatic Side Chains 1774.5 Conclusions 179References 1825 Reactive Inorganic Oxy-Species of C, N, S, and P 2055.1 Carbon Species 2065.1.1 Carbonate Radical 2065.1.1.1 Generation and Properties 2065.1.1.2 Reactivity 2105.1.2 Peroxymonocarbonate 2175.1.2.1 Reactivity 2175.1.3 Carboxyl Radical 2195.2 Nitrogen Species 2205.2.1 Nitrogen Monoxide 2205.2.2 Nitrogen Dioxide Radical 2235.2.3 Peroxynitrite 2245.2.3.1 Generation 2245.2.3.2 Decomposition in Aqueous Solution 2265.2.3.3 Reactivity with CO2 2285.2.3.4 Reactivity with Inorganic and Organic Substrates 2295.2.3.5 Reactivity with Proteins and Nonprotein Metal Centers 2315.2.3.6 Reactivity with Amino Acids, Peptides, and Proteins 2335.3 Sulfur Species 2415.3.1 Oxysulfur Radicals 2415.3.1.1 Generation 2415.3.1.2 Reactivity 2445.4 Phosphorous Species 2465.4.1 Phosphate Radicals 2465.4.1.1 Generation, Equilibria, and Spectral Characteristics 2475.4.1.2 Reactivity 2485.5 Conclusions 250References 2526 High-Valent Cr, Mn, and Fe Species 2786.1 Chromium 2796.1.1 Aqueous Chemistry of Oxo-Cr Compounds 2806.1.1.1 Cr(III) 2806.1.1.2 Cr(VI) 2806.1.1.3 Cr(III) Superoxo and Hydroperoxo Complexes 2816.1.1.4 Aqueous Cr(IV) Ion 281Acid medium 281Alkaline Medium 2826.1.1.5 Cr(V) 2836.1.2 Chromium(VI, V, and IV) Complexes 2846.1.3 Reduction of Cr(VI/V/IV) by Substrates 2856.1.4 Reactivity of Cr Species 2866.1.4.1 Fe(II) Complexes 2866.1.4.2 Hydrogen Peroxide 2876.1.4.3 Carbohydrates 2876.1.4.4 Hydroxy Acids 2876.1.4.5 Ascorbic Acid 2886.1.4.6 Catecholamines 2886.1.4.7 Thiols 2896.1.4.8 Non-Sulfur-Containing Amino Acids and Peptides 2916.1.4.9 Proteins 2916.1.4.10 NADPH/NADP 2926.1.4.11 Nitric Oxide Synthase (NOS) 2926.1.5 Mechanism 2926.1.6 Carcinogenesis 2956.1.7 Genotoxicity and Cytotoxicity 2986.1.8 Conclusions 3026.2 Manganese 3026.2.1 Aqueous Chemistry of Oxo-Mn Compounds 3056.2.1.1 Mn(III) 3056.2.1.2 Mn(IV) 3086.2.1.3 Mn(V) and Mn(VI) 3086.2.2 Reactivity of Complexes of Hypervalent Mn 3126.2.3 Oxidation by Mn(VII) 3136.2.3.1 Amino Acids 3146.2.3.2 Aminopolycarboxylates (APCs) 3196.2.4 Conclusions 3226.3 Iron 3226.3.1 Iron(IV) and Iron(V) 3256.3.1.1 Ferryl(IV) Ion 3256.3.1.2 Iron(IV)- and Iron(V)-Oxo Complexes 3306.3.1.3 Ferrate(IV) 3386.3.1.4 Ferrate(V) and Ferrate(VI) 3396.3.2 Reactivity of Ferrate(V) and Ferrate(VI) 3406.3.2.1 Amines 3416.3.2.2 Amino Acids 3436.3.2.3 Aminopolycarboxylates 3536.3.3 Conclusions 356References 357INDEX 383

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