Asymmetric reductions of ethyl 2-(benzamidomethyl)-3-oxobutanoate by yeasts |
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| Authors: | Raffaella Gandolfi Edoardo Cesarotti Francesco Molinari Diego Romano Isabella Rimoldi |
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| Institution: | 1. Università degli Studi di Milano, Institute of Organic Chemistry ‘A. Marchesini’, Via Venezian 21, 20133 Milan, Italy;2. Department of Inorganic, Metallorganic and Analytical Chemistry ‘L. Malatesta’, Via Venezian 21, 20133 Milan, Italy;3. Department of Food Science and Microbiology, Via Mangiagalli 25, 20133 Milan, Italy |
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| Abstract: | The stereoselective reduction of ethyl 2-(benzamidomethyl)-3-oxobutanoate 1 using yeasts was investigated among a restricted number (12) of yeasts. Kluyveromyces marxianus var. lactis CL69 diastereoselectively produced (2R,3S)-ethyl 2-(benzamidomethyl)-3-hydroxybutanoate 2, whereas Pichia glucozyma CBS 5766 gave (2S,3S)-2 as the major stereoisomer. The biotransformations were independently optimized for minimizing by-product formation and maximizing the diastereoselectivity. Under optimized conditions, K. marxianus var. lactis CL 69 gave the (2R,3S)-ethyl 2-(benzamidomethyl)-3-hydroxybutanoate 2 with ee > 99% and de = 98%, while P. glucozyma CBS 5766 allowed for the production of (2S,3S)-2 with ee > 99% and de = 86%. |
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