Enzyme-catalysed [4+2] cycloaddition is a key step in the biosynthesis of spinosyn A

Hak Joong Kim, Mark W. Ruszczycky, Sei-hyun Choi, Yung-nan Liu and Hung-wen Liu ()
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Hak Joong Kim: University of Texas at Austin
Mark W. Ruszczycky: College of Pharmacy, University of Texas at Austin
Sei-hyun Choi: University of Texas at Austin
Yung-nan Liu: College of Pharmacy, University of Texas at Austin
Hung-wen Liu: University of Texas at Austin

Nature, 2011, vol. 473, issue 7345, 109-112

Abstract: 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.

Date: 2011
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DOI: 10.1038/nature09981

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