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Article Dans Une Revue Green Chemistry Année : 2017

Engineering a thermostable transketolase for arylated substrates.

Résumé

Aromatic components are difficult substrates for enzymes catalyzing stereoselective carboligation reactions. We have engineered transketolase from Geobacillus stearothermophilus by directed evolution to utilize arylalkanals and benzaldehyde as the electrophilic substrate in highly stereoselective C–C bond forming conversions. Enzyme variants were discovered with rate accelerations up to 28-fold that convert 2-phenylethanal, 3-phenylpropanal, phenyloxyethanal, benzyloxyethanal, and (N-Cbz)-3-aminopropanal with formation of the corresponding aryl-substituted 1,3-dihydroxyketones in good yields (60–72%) and virtually complete (3S)-stereoselectivity (>99% ee). Novel double-site variants were also found for the conversion of benzaldehyde.

Domaines

Chimie

Dates et versions

hal-01541467 , version 1 (19-06-2017)

Identifiants

Citer

Thangavelu Saravanan, Marie-Luise Reif, Dong Yi, Marion Lorillière, Franck Charmantray, et al.. Engineering a thermostable transketolase for arylated substrates. . Green Chemistry, 2017, 19, pp.481-489. ⟨10.1039/C6GC02017H⟩. ⟨hal-01541467⟩
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