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3.6 Halogenases

DOI: 10.1055/sos-SD-216-00195

Grüschow, S.; Smith, D. R. M.; Gkotsi, D. S.; Goss, R. J. M.Science of Synthesis: Biocatalysis in Organic Synthesis, (20153313.

General Introduction

The introduction of a halogen into a molecule can be beneficial. Halogens often have profound effects on the physical properties of molecules by changing lipophilicity, electronics, and compound stability. Halogenation of a drug or agrochemical can affect bioactivity by altering the binding of drugs to their targets. Furthermore, increased lipophilicity may influence the bioavailability of a compound, and by blocking metabolic sites the half-life of the compound may be significantly increased.[‌1‌] A further use of halogens is to offer a chemical handle by which to derivatize the target compound without the need for protecting groups.[‌2‌] Nature provides many examples of halogen-containing natural products where most of the halogens are installed in a highly regiospecific manner, and some must have arisen through stereoselective enzymatic halogenation. For example, obtusenyne and maʼilione are isolated from Laurencia,[‌3‌,‌4‌] halomon from Portieria,[‌5‌] and the fimbrolides, such as 4-bromo-3-butyl-5-(dibromomethylene)furan-2(5H)-one, from Delisea[‌6‌] (Scheme 1), and further examples are given throughout this section. It is attractive to explore whether the catalytic potential that is offered by nature might be harnessed for synthetic purposes. In this section, we will briefly outline the issues of chemical halogenation, and then present an overview of the current understanding of halogenating enzymes and their applications.

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References