How Complex Terpenes Are Made

A study of how a bacterial enzyme synthesizes terpenes could lead to the more efficient production of anti-inflammatory drugs.

AsianScientist (Apr. 10, 2015) – Researchers have shed light on the precisely controlled process of terpene cyclization. The results, published in Angewandte Chemie, could lead to an improved production of anti-inflammatory compounds and other useful medicines or fragrances.

Terpenes are a class of organic compounds that are widely used in the food and pharmaceutical industries. They are produced by certain plants and insects but only in very small amounts, making them expensive to extract. Furthermore, due to their complex chemical structure, terpenes are difficult to synthesize.

A team of researchers from the University of Tokyo, Osaka City University and the Institute of Microbial Chemistry studied cyclooctat-9-en-7-ol synthase (CotB2), an enzyme from the bacteria Streptomyces melanosporofaciens that produces the anti-inflammatory compound cyclooctatin.

Using radioactively labelled glucose and geranylgeranyl diphosphate (GGDP) substrates, the group led by Professor Tomohisa Kuzuyama found that the CotB2-catalyzed reaction involves dissociation of the pyrophosphate leaving group of GGDP, an unusual carbon backbone rearrangement and a series of long-range hydride shifts.

Their results may lead to the development of novel biocatalysts useful for the production of a diverse range of complex terpene compounds that exhibit biological activity.

The article can be found at: Meguro et al. (2015) An Unusual Terpene Cyclization Mechanism Involving A Carbon-Carbon Bond Rearrangement.


Source: The University of Tokyo.
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