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The biosynthetic route to a naturally occurring insecticide, spinosyn A, has been established. One of the enzymes involved might catalyse a reaction that, although widely used by chemists, has proved elusive in nature. See Letter p.109 A 'Diels–Alderase' enzyme identified The naturally occ...

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Published inNature (London) Vol. 473; no. 7345; pp. 35 - 36
Main Author Kelly, Wendy L.
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 05.05.2011
Nature Publishing Group
Subjects
639/638/45
639/638/92/60
Biosynthesis
Chemical bonds
Enzymes
Humanities and Social Sciences
multidisciplinary
Natural products
news-and-views
Science
Science (multidisciplinary)
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Summary:The biosynthetic route to a naturally occurring insecticide, spinosyn A, has been established. One of the enzymes involved might catalyse a reaction that, although widely used by chemists, has proved elusive in nature. See Letter p.109 A 'Diels–Alderase' enzyme identified The naturally occurring compound spinosyn A is a component of several environmentally benign commercial insecticides. How its tetracyclic ring system is biosynthesized has been a subject of much speculation. One possible mechanism is the Diels–Alder reaction, a [4+2] cycloaddition reaction in which a cyclohexene ring is formed between a conjugated diene and an electron-deficient alkene via a single pericyclic transition state. This reaction is a rarity in nature, but a structural and kinetic study of the enzyme SpnF from the soil bacterium Saccharopolyspora spinosa now identifies it as perhaps the first stand-alone enzyme to merit the name 'Diels–Alderase', solely committed to the catalysis of a [4+2] cycloaddition reaction with an estimated 500-fold rate enhancement.
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ISSN:0028-0836
1476-4687
DOI:10.1038/473035a