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Organic Chemicals in the Environment

Mechanisms of Degradation and Transformation, Second Edition

By Alasdair H. Neilson, Ann-Sofie Allard

CRC Press – 2012 – 1,047 pages

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    978-1-43-982637-9
    September 4th 2012

Description

Addressing the persistent environmental threat of organic chemicals with a fresh approach to degradation and transformation processes, Organic Chemicals in the Environment: Mechanisms of Degradation and Transformation, Second Edition examines a wide range of compounds as well as abiotic and microbiological reactions mediated by microorganisms. The book emphasizes the pathways used and the broad classes of enzymes involved. It provides an overview of experimental procedures with detailed coverage of the organic compounds that are considered to be xenobiotics.

The book begins by providing a broad perspective on abiotic and biotic reactions, including the significance of a range of environmental determinants. The following chapters briefly introduce experimental procedures and emphasize those procedures for establishing the structure of metabolites using isotopes and physical methods. Next, the authors outline details of biochemical reactions involved in the biodegradation of the major groups of aliphatic, carbocyclic aromatic, and heterocyclic compounds. They end with coverage of bioremediation that has attracted increasing concern because of the hazard presented by the disposal of unwanted chemicals or by-products from their manufacture.

Broad and comprehensive, this book provides a cohesive treatment of the subject. It contains an extensive set of literature references and numerous illustrative figures. The authors use a mechanistic approach with emphasis on the pathways, and the principles that emerge provide a guide not only for specific compounds but also for those having a more remote structural resemblance.

Reviews

"Now in its second edition, this large work is packed with useful and pertinent information concerning the potential fate of chemicals that have made their way, usually unintentionally, into the surrounding biosphere. … As usual with such books, the layout is neat and the print easy to read. Many chemical schemes and copious references after (and within) each chapter add to the work. Good quality paper, firm binding and an overall solid construction ensure that this book will remain durable for many years. For anyone with an interest in xenobiotics and environmental issues this book certainly is a useful reference source."

—Steve Mitchell, Faculty of Medicine, Imperial College London, UK, 2013

Praise for the First Edition:

Broad and comprehensive, this book provides a cohesive treatment of the subject. It contains an extensive set of literature references and numerous illustrative figures.

—J. Albaigés, CID-CSIC, Journal of Environmental Analytical Chemistry, Feb. 2008

Contents

Degradation and Transformation Processes

Abiotic Reactions: An Outline

Introduction

Photochemical Reactions in Aqueous and Terrestrial Environments

The Diversity of Photochemical Transformations

Hydroxyl Radicals in the Destruction of Contaminants

Other Photochemically Induced Reactions

The Role of Humic Matter: Singlet Dioxygen

Interactions between Photochemical and Other Reactions

Reactions in the Troposphere

Reentry of Tropospheric Transformation Products

Chemically Mediated Transformations

Reductive Dehalogenation

Thiol and Sulfide Reductants

Sonication

References

Biotic Reactions: An Outline of Reactions and Organisms

Microbial Reactions

Introduction

Definitions: Degradation and Transformation

Biodegradation of Enantiomers: Racemization

Sequential Microbial and Chemical Reactions

The Spectrum of Organisms

Microbial Metabolism of CCompounds

Anaerobic Bacteria

Organisms from Extreme Environments: Extremophiles

Eukaryotic Microorganisms

References

Reactions Mediated by Other Biota

Aquatic and Terrestrial Biota

Metabolism by Fish

Metabolism by Other Organisms

References

Plants and Their Microbial Interactions

Introduction

Primary Roles of Plants

Secondary Role of Plants

Plant Metabolites as Antagonists

Group

Group II Phytoalexins

Roles of Bacteria Including Biocontrol Agents

Plant Endophytes

Microorganisms with Activity as Biocontrol Agents

Siderophores in Plants: Roles of Iron

The Role of Mycorrhizal and Other Fungi

Conclusions

References

Mechanisms

Oxidation, Dehydrogenation, and Reduction

Introduction

Monooxygenation

References

Dioxygenation

References

Oxidases, Peroxidases, and Haloperoxidases

References

Incorporation of Oxygen from Water: Hydrolases, Oxidoreductases, and Hydratases

References

Electron Acceptors Other than Oxygen

References

Dehydrogenation

References

Reductases and Related Enzymes

References

Non-Redox Reactions

Pyridoxal-′-Phosphate (PLP)-Dependent Reactions

References

Glutathione-Dependent Reactions

References

Corrinoid-Dependent Reactions

References

Free-Radical Reactions

References

Coenzyme A: Ligase, Transferase, Synthetase

References

Metalloenzymes

Enzymes Containing Manganese, Iron, Cobalt, Copper, Zinc, Molybdenum, Tungsten, and Vanadium

References

Interactions

Environmental Stress

Adaptation to Stress

Physical Stress

References

Chemical Stress

Enzymatic Covalent Modification of Antibiotic: Range of Reactions

Efflux Systems

References

Metabolic Interactions

Single Substrates: Several Organisms

Cometabolism and Related Phenomena

Induction of Catabolic Enzymes

Role of Readily Degraded Substrates

Association of Bacteria with Particulate Material: "Free" and "Bound" Substrates

Substrate Concentration, Transport into Cells, and Toxicity

Preexposure: Pristine and Contaminated Environments

Rates of Metabolic Reaction

Metabolic Aspects: Nutrients

Regulation and Toxic Metabolites

Catabolic Plasmids

References

Experimental Procedures

Experimental Procedures

General

Introduction

Abiotic Reactions

Microbial Reactions

Storage of Samples

Determination of Ready Biodegradability

Design of Experiments on Inherent Biodegradability

Organic Substrates

Techniques for Anaerobic Bacteria

Design of Experiments on Biodegradation and Biotransformation

Pure Cultures and Stable Consortia

Cell Growth at the Expense of the Xenobiotic

Stable Enrichment Cultures

Use of Dense Cell Suspensions

Use of Immobilized Cells

Application of Continuous Culture Procedures

Simultaneous Presence of Two Substrates

Use of Unenriched Cultures: Undefined Natural Consortia

Microcosm Experiments

Experiments in Models of Natural Aquatic Systems

Evaluation of Degradation Using Metabolites

Experimental Problems: Water Solubility, Volatility, Sampling, and Association of the Substrate with Microbial Cells

References

Study of Microbial Populations

Introduction

Analysis of Degradative Populations

Procedures Directed to Populations for the Degradation of Specific Contaminants

Application to Populations of Specific Groups of Organisms

Nonspecific Examination of Natural Populations

References

Procedures for Elucidation of Metabolic Pathways

Introduction

Application of Natural and Synthetic Isotopes

Carbon (C and C)

Sulfur (S) and Chlorine (Cl)

Hydrogen (H) and Oxygen (O)

Other Isotopes

Isotope Effects and Stable Isotope Fractionation

References

Stable Isotope Probes and Stable Isotope Fractionation

Experimental Procedures

Expression of Results

Stable Isotope Probes

Application to Processes

Application to Biodegradation

Stable Isotope Fractionation

References

Physical Methods of Structure Determination

Nuclear Magnetic Resonance

References

Electron Paramagnetic Resonance

References

X-Ray Crystallographic Analysis

Acetylene Hydratase

Triesterase

Dehydrogenases

Quinoprotein Amine Oxidase

Dehalogenases

Atypical Dehydratases

Arsenite Oxidase

Methyl Coenzyme M Reductase

Urease

Hydrogenase

β-Lactamases

Alkylsulfatase

Dioxygenases

Superoxide Dismutase

Formyl-CoA Transferase

PLP-Independent Racemases

References

Pathways and Mechanisms of Degradation and Transformation

Aliphatic Compounds

Alkanes

References

Cycloalkanes: Including Terpenoids and Steroids

References

Alkenes and Alkynes

References

Alkanols, Alkanones, Alkanoates, Amides

References

Alkylamines and Amino Acids

Amino Acids

References

Alkanes, Cycloalkanes, and Related Compounds with Chlorine, Bromine, or Iodine Substituents

Chlorinated, Brominated, and Iodinated Alkanes, Alkenes, and Alkanoates

References

Fluorinated Aliphatic Compounds

References

Carbocyclic Aromatic Compounds without Halogen Substituents

Monocyclic Aromatic Hydrocarbons

Introduction: Bacteria

Monocyclic Arenes

Fungi

References

Polycyclic Aromatic Hydrocarbons

Introduction

Aerobic Reactions Carried Out by Bacteria

PAHs with Three or More Rings

Anaerobic Degradations Carried Out by Bacteria

Fungal Transformations

Yeasts and Algae

White-Rot Fungi

References

Aromatic Carboxylates, Carboxaldehydes, and Related Compounds

Introduction

Benzoates

Hydroxybenzoates and Related Compounds

Mechanisms for Fission of Oxygenated Rings

Aerobic Reduction of Arene Carboxylates

Arenes with an Oxygenated Cor CSide Chain

Aldehydes

References

Nonhalogenated Phenols and Anilines

Phenols

Alkylated Phenols: Degradation of Methylcatechols

Polyhydric Phenols

Anaerobic Degradation

References

Halogenated Arenes and Carboxylates with Chlorine, Bromine, or Iodine Substituents

Arenes and Carboxylated Arenes with Halogen, Sulfonate, Nitro, and Azo Substituents

Aerobic Degradation

Anaerobic Conditions

Polychlorinated Biphenyls

Polybrominated Biphenyls and Diphenylmethanes

Mechanisms for the Ring Fission of Substituted Catechols

Halogenated Phenylacetates

References

Halogenated (Chlorine, Bromine, and Iodine) Phenols and Anilines

Phenols

O- and S-methylation

Fungi and Yeasts

Anilines

References

Fluorinated Hydrocarbons, Carboxylates, Phenols, and Anilines

Fluorinated Aromatic Hydrocarbons

Fluorobenzoates

-Fluorocinnamate

Difluorobenzoates

Fluorinated Phenols

Aromatic Trifluoromethyl Compounds

References

Arene Sulfonates

References

Aromatic Compounds with Nitro Substituents

Nitroarenes

Nitrobenzoates

Nitrophenols

References

Azoarenes

References

Heterocyclic Aromatic Compounds

Azaarenes

Five-Membered Monocyclic Aza, Oxa, and Thiaarenes

Aerobic Conditions

Indole and -Alkylindoles

Carbazole

Purines

Triazines

References

Oxaarenes

Aerobic Conditions

Fungal Reactions

References

Thiaarenes: Benzothiophenes, Dibenzothiophenes, and Benzothiazole

Benzothiophene and Dibenzothiophene

Benzothiazole

References

Miscellaneous Compounds

Carboxylate, Sulfate, Phosphate, and Nitrate Esters

Carboxylates

Sulfates

Phosphates

Nitrates

References

Ethers and Sulfides

Aliphatic and Benzylic Ethers

Aryl Ethers

References

Sulfides, Disulfides, and Related Compounds

References

Aliphatic Nitramines and Nitroalkanes

Nitramines

Nitroalkanes

References

Aliphatic Phosphonates and Sulfonates

Introduction

Phosphonates

Sulfonates

Boronates

References

Degradation of Organic Compounds of Metals and Metalloids

Tin

Lead

Mercury

Arsenic

References

Index

Author Bio

Alasdair H. Neilson was Principal Scientist until retirement from IVL Swedish Environmental Research Institute in Stockholm. He studied chemistry at the University of Glasgow and took his Ph.D. in organic chemistry in Alexander Todd's laboratory at Cambridge University. He carried out further research at Cambridge University in organic chemistry, and in theoretical chemistry with Charles Coulson at Oxford University. He held academic positions in the universities of Glasgow and Sussex, and obtained industrial experience in the pharmaceutical industry. He consolidated his experience by turning to research in microbiology during a prolonged stay with Roger Stanier and Mike Doudoroff at the University of California, Berkeley. His interests have ranged widely and included studies on nitrogen fixation, carbon and nitrogen metabolism in algae, and various aspects of environmental science including biodegradation and biotransformation, chemical and microbiological reactions in contaminated sediments, and ecotoxicology. With his group of collaborators, these studies have resulted in publications in Applied and Environmental Microbiology, Journal of Chromatography, Environmental Science & Technology, and Ecotoxicology & Environmental Safety, and in chapters contributed to several volumes of The Handbook of Environmental Chemistry. He is a member of the American Chemical Society, the American Society for Microbiology, the American Society of Crystallography, and the American Association for the Advancement of Science (AAAS).

Ann-Sofie Allard studied as a chemical microbiologist and is currently a Senior Microbiologist at IVL Swedish Environmental Research Institute in Stockholm. She has carried out research on a wide range of water quality issues including the distribution of Yersinia enterocolitica in Swedish freshwater systems, and processes for the removal of hormone disrupters. She has carried out extensive studies on the biodegradation and biotransformation of organic contaminants, and in ecotoxicology, and she has implemented independent studies on the uptake and metabolism of organic contaminants and metals in higher plants in the context of bioremediation. Her studies have been published in Applied and Environmental Microbiology, International Biodeterioration and Biodegradation, Environmental Chemistry and Ecotoxicology, and Journal of Environmental Science and Health, and in chapters contributed to several volumes of The Handbook of Environmental Chemistry. She is a member of the American Chemical Society.

Name: Organic Chemicals in the Environment: Mechanisms of Degradation and Transformation, Second Edition (Hardback)CRC Press 
Description: By Alasdair H. Neilson, Ann-Sofie Allard. Addressing the persistent environmental threat of organic chemicals with a fresh approach to degradation and transformation processes, Organic Chemicals in the Environment: Mechanisms of Degradation and Transformation, Second Edition examines a wide...
Categories: Organic Chemistry, Chemical Engineering, Natural Hazards & Risk