2nd Edition

Organic Chemicals in the Environment
Mechanisms of Degradation and Transformation, Second Edition




ISBN 9781439826379
Published September 5, 2012 by CRC Press
1047 Pages 415 B/W Illustrations

USD $230.00

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Book 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.

Table of 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

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Author(s)

Biography

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.

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