1st Edition

Handbook of Biotransformations of Aromatic Compounds

By B.L. Goodwin Copyright 2005
    2124 Pages
    by CRC Press

    Understanding the biotransformations of aromatic compounds and how they metabolize in animals, plants, and microbes, is central to the applications in a wide range of industries, such as the design and testing of natural and synthetic pharmaceuticals, oil refining, the development of agrochemicals, bioremediation, and for use in functional genomics and xenobiotics.

    Presenting the most complete resource of its kind, the Handbook of Biotransformations of Aromatic Compounds examines 20,000 aromatic compounds researched since 1972, and assembled from all the major, relevant journals. The author focuses his coverage on the biotransformation in animals, plants, and microbes while remaining within the scope of aromatic compounds that contain, or are fused with, at least one aromatic C6 ring. Part One lists each compound alphabetically along with the forward and reverse mechanisms of its metabolism in specific organisms. Part Two characterizes the different types of organic reactions that have been identified - including formation and degradation, oxidations and reductions, substitution, and transfer reactions - and the enzymes associated with those reactions. The author cites selected references for enzymes that are well documented while filling in the details for those with little research literature. This book also contains a searchable CD-ROM of the author's previous work covering aromatic compounds researched from 1900 through 1972.

    Presenting the most complete resource of its kind, this well-established author draws on his firsthand knowledge to organize a large body of information into a user-friendly and indispensable handbook for professionals, policymakers, and researchers alike.

    PART 1
    Alphabetical Listing of Aromatic Compounds

    PART 2
    REACTIONS INVOLVING THE FORMATION AND DEGRADATION OF THE AROMATIC NUCLEUS
    Aromatization of 6-membered carbon and heterocyclic rings
    Formation of carbon ring systems
    Formation of heterocyclic ring systems
    Polymerization reactions
    Reactions involving carbon ring fission
    Reactions involving heterocyclic ring fission
    Dearomatization
    Ring expansion

    OXIDATIONS AND REDUCTIONS INVOLVING THE AROMATIC NUCLEUS AND NON-ORGANIC SUBSTITUENTS
    Hydroxylation of the aromatic nucleus
    Formation of quinones and analogues from catechols, quinols and other precursors
    Free radicals from phenols
    Oxidation of nuclear amino groups and analogues
    Oxidation of heterocyclic amines
    Reduction of nitro groups and analogues
    Oxidation and reduction of sulphur atoms
    Reduction of quinones and analogues
    Halogens and the aromatic nucleus
    Epoxide formation and reduction
    Deamination of arylamines without hydroxylation
    Dehydroxylation of phenols
    Nitro group addition and removal

    OXIDATIONS AND REDUCTIONS OF SUBSTITUENT SIDE CHAINS AND NON-AROMATIC RING SYSTEMS (WITHOUT ALTERING CHAIN LENGTH)
    Hydroxylation of the carbon side-chain
    Alkyl oxidation to ketone
    Oxidations and reductions of alcohols, aldehydes and ketones
    Reductions of acids
    Deamination
    Oxidative removal of substituents on amino groups
    Oxidations and reductions involving nitrogen atoms
    O-Dealkylation
    Oxidations and reductions of non-aromatic ring systems
    Sulphur replacement
    Dehydroxylation
    Side chain halogenation
    Oxidative rearrangement

    FORMATION AND DEGRADATION OF SIDE-CHAINS
    Side-Chain Formation
    Decarboxylation of phenolic groups without hydroxylation
    Decarboxylation reactions of side-chains
    Other reactions involving side-chain shortening and removal
    Chain lengthening reactions

    CONJUGATION AND SUBSTITUTION REACTIONS
    Ester formation
    Sulphamate formation
    Glycoside formation
    Conjugation of thiols
    Formation of amides and substituted amides
    Phosphorylation reactions
    Ether formation
    N-alkylation
    Silane anhydrides

    ELIMINATION OF SUBSTITUENTS
    Ester hydrolysis
    Hydrolysis of glycosides
    Hydrolysis of amides
    Hydrolysis of phosphates
    Miscellaneous reactions

    TRANSFER REACTIONS
    Transamination
    Isomerization
    Migrations
    Racemization

    FORMATION AND REACTIONS OF NON-ARYL DOUBLE AND TRIPLE BONDS
    Double and triple bond formation
    Reactions of double bonds

    HYDRATION OF EPOXIDES

    LIGHT-FORMING REACTIONS

    INDEX

    BIBLIOGRAPHY

    Biography

    B.L. Goodwin

    "The book is indispensable for my work, and for researchers involved in a variety of fields in academia and industry…The author is a world authority on the subject…I HIGHLY recommend this book…"
    - Dr. Iqbal Gill, Head of Biotransformations/Biocatalysis Department, Roche Vitamins Inc.

    "…a well-structured book covering the literature of the last thirty years….easy to use and contains plenty of interesting material…contains an immense amount of information on themetabolism of aromatic compounds."
    ChemBioChem 2005, volume 6

    "This book is an excellent and exhaustive source…a labour of love which should prove to be an essential reference source for those involved in the biotransformation of aromatics as it provides detailed coverage of developments within this field over the past 100 years."

    biochemist.org, July 8, 2005