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2003 | OriginalPaper | Chapter

Biological Effects and Biosynthesis of Brominated Metabolites

Author : Alasdair H. Neilson

Published in: Organic Bromine and Iodine Compounds

Publisher: Springer Berlin Heidelberg

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On the basis of halogenated metabolites assembled by Gribble, an attempt is made to provide a hypothesis for the biosynthesis of representative groups. Examples of brominated and iodinated metabolites are drawn from the major classes of terpenoids and acetogenins, and related to the biosynthesis of their putative precursors. Brominated and iodinated carbocyclic and heterocyclic aromatic compounds are discussed as well as mechanisms for the oxidative coupling of phenolic substrates. A few chlorinated metabolites are introduced for additional illustration. Halogenation by cationoid (Hal+) reactions catalyzed by haloperoxidases is discussed, and attention drawn to the alternative role of anionoid (Hal-) halogenation. The presentation is extended to the biosynthesis of isonitriles and dichloroimines by anionoid reaction of precursors with cyanide. The range of biota that produce brominated substrates is briefly indicated, and comments made on the ecological significance of metabolites and associations among biota.

Metadata
Title
Biological Effects and Biosynthesis of Brominated Metabolites
Author
Alasdair H. Neilson
Copyright Year
2003
Publisher
Springer Berlin Heidelberg
DOI
https://doi.org/10.1007/978-3-540-37055-0_2