CuII ‐Containing 1‐Aminocyclopropane Carboxylic Acid Oxidase Is an Efficient Stereospecific Diels–Alderase

Wadih Ghattas (1) , Virginie Dubosclard (1) , Sybille Tachon (2) , Morane Beaumet (1) , Régis Guillot (1) , Marius Réglier (2) , A. Jalila Simaan (2) , Jean‐pierre Mahy (1)

1 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay
2 ISM2 - Institut des Sciences Moléculaires de Marseille

In the context of developing eco-friendly chemistry, artificial enzymes are now considered as promising tools for synthesis. They are prepared in particular with the aim to catalyze reactions that are rarely, if ever, catalyzed by natural enzymes. We discovered that 1aminocyclopropane carboxylic acid oxidase reconstituted with Cu(II) served as an efficient artificial Diels-Alderase. The kinetic parameters of the catalysis of the cycloaddition of cyclopentadiene and 2azachalcone were determined (KM = 230 µM, kapp = 3 h-1), which gave access to reaction conditions that provided quantitative yield and >99 % ee of the (1S,2R,3R,4R) product isomer. This unpreceded performance was rationalized by molecular modeling as only one docking pose of 2-azachalcone was possible in the active site of the enzyme and it was the one that leads to the (1S,2R,3R,4R) product isomer.

Domaines: Catalyse; Chimie inorganique; Sciences du Vivant [q-bio]

Wadih Ghattas, Virginie Dubosclard, Sybille Tachon, Morane Beaumet, Régis Guillot, et al.. CuII ‐Containing 1‐Aminocyclopropane Carboxylic Acid Oxidase Is an Efficient Stereospecific Diels–Alderase. Angewandte Chemie, 2019, 131 (41), pp.14747-14751. ⟨10.1002/ange.201909407⟩. ⟨hal-02299031⟩