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Handbook of Biotransformations of Aromatic Compounds




ISBN 9780415271769
Published November 10, 2004 by CRC Press
2128 Pages

 
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Book Description

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.

Table of Contents

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

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Reviews

"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