Asymmetric reduction of ketones using recombinant E. coli cells that produce a versatile carbonyl reductase with high enantioselectivity and broad substrate specificity

Ema, Tadashi; Yagasaki, Hideo; Okita, Nobuyasu; Takeda, Masahiro; Sakai, Takashi

doi:10.1016/j.tet.2006.04.061

Cited by 81 publications

(34 citation statements)

References 43 publications

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“…There are extensive works on the asymmetric reduction reaction catalyzed by whole cell with excellent enantioselectivity and yield [4,6,11]. However, the previous reported works mainly focus on application microbial organism as the biocatalyst [11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Yang

Zeng

Yang

et al. 2008

J Ind Microbiol Biotechnol

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As an important organic compound, chiral alcohols are the key chiral building blocks to many single enantiomer pharmaceuticals. Asymmetric reduction of the corresponding prochiral ketones to produce the chiral alcohols by biocatalysis is one of the most promising routes. Asymmetric reduction of different kinds of non-natural prochiral ketones catalyzed by various plants tissue was studied in this work. Acetophenone, 4'-chloroacetophenone and ethyl 4-chloroacetoacetate were chosen as the model substrates for simple ketone, halogen-containing aromatic ketone and beta-ketoesters, respectively. Apple (Malus pumila), carrot (Daucus carota), cucumber (Cucumis sativus), onion (Allium cepa), potato (Soanum tuberosum), radish (Raphanus sativus) and sweet potato (Ipomoea batatas) were chosen as the biocatalysts. It was found that these kinds of prochiral ketoness could be reduced by these plants tissue with high enantioselectivity. Both R- and S-form configuration chiral alcohols could be obtained. The e.e. and chemical yield could reach about 98 and 80% respectively for acetophenone and 4'-chloroacetophenone reduction reaction with favorable plant tissue. And the e.e. and yield for ethyl 4-chloroacetoacetate reduction reaction was about 91 and 45% respectively.

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Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Yang

Zeng

Yang

et al. 2008

J Ind Microbiol Biotechnol

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show abstract

“…[26a] 22, [30] 23, [31] 24, [32] 25, [33] 26, [34] 27, [35] 28, [36] 31-d 1 , [37] 32, [38] 33, [18] 34, [19] and 1-d 1 .…”

Section: Methodsmentioning

confidence: 99%

Radical Reduction of Epoxides Using a Titanocene(III)/Water System: Synthesis of β‐Deuterated Alcohols and Their Use as Internal Standards in Food Analysis

et al. 2010

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We describe a comprehensive study into the Cp2TiCl‐mediated reductive epoxide ring opening using either water as a hydrogen source or deuterium oxide as a deuterium source. The remarkable chemical profile of this reaction allows access to alcohols with anti‐Markovnikov regiochemistry from different epoxides. The use of D2O as a deuterium source leads to an efficient synthesis of β‐deuterated alcohols, including a deuterated sample of tyrosol, a bioactive compound contained in the leaves of the olive, which was successfully applied as an internal standard in food analysis.

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“…In one type, enzymes use similar substrates to perform a single chemical reaction (Nobeli et al, 2009). This indicates that most enzymes accept some alternative substrates that are generally similar to normal substrates (Zhu et al, 2006;Ema et al, 2006;Itoh et al, 2004). Substrate promiscuity of enzymes is regarded as a cornerstone of catalysis and affects the procedures by which proteins are characterized biochemically (Khersonsky and Tawfik, 2010).…”

Section: Substrate Specificitymentioning

confidence: 99%

Purification and characterization of a novel NADH-dependent carbonyl reductase from Pichia stipitis involved in biosynthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate

Cao

et al. 2011

Bioresource Technology

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Asymmetric reduction of ketones using recombinant E. coli cells that produce a versatile carbonyl reductase with high enantioselectivity and broad substrate specificity

Cited by 81 publications

References 43 publications

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Radical Reduction of Epoxides Using a Titanocene(III)/Water System: Synthesis of β‐Deuterated Alcohols and Their Use as Internal Standards in Food Analysis

Purification and characterization of a novel NADH-dependent carbonyl reductase from Pichia stipitis involved in biosynthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate

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