Oxidation of Amino Acids, Peptides, and Proteins Kinetics and Mechanism

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 243^rd 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

Introduction

1.  Reactive Species

1.1.  Diseases

1.1.1 Neurodegenerative Diseases

1.1.1.1  Alzheimer’s Disease

1.1.1.2  Parkinson’s Disease

1.1.2  Metals in Human Diseases

1.2  Protein Structure

1.2.1  Oxidative Labeling

1.2.1.1  Carbonyls labeling

1.2.1.2  Cysteine residues labeling

1.2.1.3  Reactive species labeling

1.2.1.4  Hydroxyl Radical Labeling

1.2.2. Other techniques

1.3  Reactive Species

1.3.1  Halogen Species

1.3.2  Oxygen Species

1.3.3  Nitrogen Species

1.3.4  Sulfur Species

1.3.5  High-Valent Cr, Mn, and Fe Species

1.4  Reactive Species in Environmental processes             

1.4.1  Atmospheric Environment

1.4.2  Disinfection By-Products

1.4.3  Oxidation Processes for Purifying Water

2.  Acid-Base Properties

2.1  Dissociation Constants

2.2 Speciation

2.2.1  Protonation

2.2.2  Metal Complexes

2.2.2.1. Iron

2.2.2.2. Copper, Zinc, and Nickel

3.  Halogenated species

3.1 Hypohalogens

3.1.1 Hypochlorite

3.1.1.1 Kinetics of HOCl

3.1.1.2 Products of HOCl Oxidation

3.1.2 Hypobromite

3.1.2.1 Kinetics of HOBr

3.1.2.2   Products of HOBr Oxidation

3.1.3 Hypothiocyanous

3.1.3.1 Kinetics of HOSCN

3.1.3.2 Products of HOSCN

3.2  Halamines

3.2.1 Hydrolysis of Halamines

3.2.2 Halogen transfer by Halamines

3.2.3  Reduction of Halamines

3.3 Chlorine Dioxide

3.3.1  Generation of ClO2

3.3.2 Decomposition of ClO2

3.3.3 Reactivity of ClO2

3.3.3.1 Amino Acids, peptides, and proteins

3.4.  Conclusions

4. Reactive Oxygen Species

4.1  Superoxide

4.1.1 Generation

4.1.2. Properties

4.1.3  Reactivity

4.1.4  Metalloenzymes

4.1.4.1  Manganese Superoxide Dismutase

4.1.4.2  Iron Superoxide Dismutase

4.1.4.3  Iron Superoxide Reductase

4.2  Singlet Oxygen

4.2.1 Reactivity

4.3  Ozone

4.3.1 Reactivity

4.4  Hydroxyl Radical

4.4.1. Generation

4.4.2  Reactivity

4.4.2.1 Main Chain Cleavage of Protein

4.4.2.2  Oxidation of Amino Acid Side Chains

4.4.2.2.1  Aliphatic Side Chains

4.4.2.2.2  Sulfur-Containing Side Chains

4.4.2.2.3  Acidic Side Chains

4.4.2.2.4  Basic Side Chains

4.4.2.2.5  Aromatic Side Chains

4.5. Conclusions

5.  Reactive Inorganic Oxy-Species of C, N, S, and P

5.1.  Carbon Species

5.1.1.  Carbonate Radical

5.1.1.1   Generation and properties

5.1.1.2   Reactivity

5.1.2. Peroxymonocarbonate

5.1.2.1  Reactivity

5.1.3.  Carboxyl Radical

5.2  Nitrogen Species

5.2.1.  Nitrogen Monoxide

5.2.2.  Nitrogen Dioxide Radical

5.2.3.  Peroxynitrite

5.2.3.1   Generation

5.2.3.2  Decomposition in Aqueous Solution

5.2.3.3  Reactivity with CO2

5.2.3.4 Reactivity with inorganic and organic substrates

5.2.3.5 Reactivity with Proteins and Non-Protein Metal Centers

5.3  Sulfur Species

5.3.1  Oxy-Sulfur Radicals

5.3.1.1   Generation

5.3.1.2   Reactivity

5.4  Phosphorous Species

5.4.1 Phosphate Radicals

5.4.1.1   Generation, Equilibria, and Spectral Characteristic

5.4.1.2 Reactivity

5.5.  Conclusions

6. High-Valent Cr, Mn, and Fe Species

6.1  Chromium

6.1.1  Aqueous Chemistry of Oxo-Cr Compounds

6.1.1.1.  Cr(III)

6.1.1..2.  Cr(VI)

6.1.1.3.  Cr(III) Superoxo and Hydroperoxo Complexes

6.1.1.4.  Aqueous Cr(IV) Ion

6.1.1.4.1.  Acid  medium

6.1.1.4.2.  Alkaline  medium

6.1.1.5.  Cr(V)

6.1.2.  Chromium(VI,V, and IV) Complexes

6.1.3.  Reduction of Cr(VI/V/IV) by Substrates

6.1.4.  Reactivity of Cr Species

6.1.4.1   Fe(II) Complexes

6.1.4.2   Hydrogen peroxide

6.1.4.3   Carbohydrates

6.1.4.4   Hydroxyacids

6.1.4.5   Ascorbic acid

6.1.4.6   Catecholamines

6.1.4.7   Thiols

6.1.4.8   Non-Sulfur-Containing Amino Acids and Peptides

6.1.4.9   Proteins

6.1.4.10 NADPH/NADP

6.1.4.11 Nitric oxide synthase

6.1.5.  Mechanism

6.1.6   Carcinogenesis

6.1.7   Genotoxicity and Cytotoxicity

6.1.8  Conclusions

6.2  Manganese

6.2.1  Aqueous Chemistry of Oxo-Mn Compounds

6.2.1.1. Mn(III)

6.2.1.2. Mn(IV)

6.2.1.3. Mn(V) and Mn(VI)

6.2.2.  Reactivity of Complexes of Hypervalent Mn

6.2.3   Oxidation by Mn(VII)

6.2.3.1   Amino Acids

6.2.3.2   Aminopolycarboxylates

6.2.4  Conclusions

6.3. Iron

6.3.1 Iron(IV) and Iron(V)

6.3.1.1   Ferryl(IV)

6.3.1.2 Iron(IV)- and Iron(V)-Oxo Complexes

6.3.1.3 Ferrate(IV)

6.3.1.4. Ferrate(V) and Ferrate(VI)

6.3.2 Reactivity of Ferrate(V) and Ferrate(VI)

6.3.2.1. Amines

6.3.2.2. Amino Acids

6.3.2.3 Aminopolycarboxylates

6.3.3.  Conclusions

Index

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