- Structure-Guided Directed Evolution of a Carbonyl Reductase Enables the Stereoselective Synthesis of (2 S,3 S)-2,2-Disubstituted-3-hydroxycyclopentanones via Desymmetric Reduction
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In this study, an engineered carbonyl reductase (M4) was obtained through structure-guided directed evolution of a carbonyl reductase (SSCR) from Sporobolomyces salmonicolor AKU4429. Mutant M4 showed 23.9-fold enhancement of enzyme activity toward the model substrate 2-methyl-2-benzyl-1,3-cyclopentanedione, affording the (2S,3S)-stereoisomer in >98percent ratio. This variant also showed excellent stereoselectivity toward most of the tested substrates, offering a valuable biocatalyst for the stereoselective reduction of these cyclic diketones to access the corresponding (2S,3S)-2,2-disubstituted-3-hydroxyketones.
- Li, Juan,Feng, Jinhui,Chen, Xi,Gong, Jingyao,Cui, Yunfeng,Zhang, Hongliu,Bu, Dandan,Wu, Qiaqing,Zhu, Dunming
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- Comparative reductive desymmetrization of 2,2-disubstituted-cycloalkane-1,3-diones
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Reductive desymmetrization of 2-methyl-2-substituted-cycloalkane-1,3-diones can be effected using either NaBH4 in DME or lithium tri-tert-butoxyaluminum hydride (LTBA) in THF at -60 °C. The former is a new approach that offers slightly greater
- Carr, Jeremy M.,Snowden, Timothy S.
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p. 2897 - 2905
(2008/09/20)
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- Highly stereocontrolled reduction of 1,3-cyclopentanediones using oxazaborolidine -BH3
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Highly enantioselective reduction of 1,3-cyclopentanediones was conducted using an oxazaborolidine derived from L-threonine and a borane complex to give either 1,3-cyclopentanediols or 3-hydroxycyclopentanones in high enantiomeric purity by choosing appropriate reduction conditions. Copyright (C) 2000 Elsevier Science Ltd.
- Shimizu, Makoto,Yamada, Shunsuke,Fujita, Yoshifumi,Kobayashi, Fumiko
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p. 3883 - 3886
(2007/10/03)
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- Asymmetric Microbial Reduction of Prochiral 2,2-Disubstituted Cycloalkanediones
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Asymmetric microbial reduction of a series of 2,2-disubstituted 1,3-cycloalkanediones with bakers' yeast was examined as an example of an enzyme-catalyzed distinction of a substrate containing two trigonal carbonyl centers with stereoheterotropic faces an
- Brooks, Dee W.,Mazdiyasni, Hormoz,Grothaus, Paul G.
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p. 3223 - 3232
(2007/10/02)
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