Development of an Efficient and Cost-Effective Enzymatic Process for Production of (R)-[3,5-bis(trifluoromethyl)phenyl] Ethanol Using Carbonyl Reductase Derived from Leifsonia sp. S749

Tang, Jiawei; Wei, Teng-Yun; Ni, Guowei; Guo, Xiang; Wu, Yuanjie; Zhang, Fuli; Chen, Shaoxin

doi:10.1007/s12010-018-2904-2

Cited by 9 publications

(7 citation statements)

References 27 publications

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“…As the key synthetic precursor of this drug, ( R )-1-(3,5-bis(trifluoromethyl) phenyl) ethanol (( R )-3,5-BTPE, 307 ) has attracted significant synthetic attention (Scheme b). Chen and co-workers described a simple and inexpensive way to synthesize this chiral intermediate using recombinant whole cell Escherichia coli overexpressing KR01 after optimization of reaction parameters employing response surface analysis . Results showed that 600 g/L 3′,5′-bis(trifluoromethyl) acetophenone ( 306 ) was reduced to ( R )-3,5-BTPE 307 with >99.9% ee and 98.3% conversion under optimized reaction conditions (Scheme b, condition 1).…”

Section: Biocatalysismentioning

confidence: 99%

“…Chen and co-workers described a simple and inexpensive way to synthesize this chiral intermediate using recombinant whole cell Escherichia coli overexpressing KR01 after optimization of reaction parameters employing response surface analysis. 209 Results showed that 600 g/L 3′,5′-bis(trifluoromethyl) acetophenone (306) was reduced to (R)-3,5-BTPE 307 with >99.9% ee and 98.3% conversion under optimized reaction conditions (Scheme 68b, condition 1). Enzyme KRED-NAD + (Scheme 68b, condition 2) 210 were also applicable for the reduction of ketone 306, leading to the production of enantio-enriched alcohol 307 at a hundred-gram scale.…”

Section: Oxidoreductasesmentioning

confidence: 99%

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Enantioselective Transformations in the Synthesis of Therapeutic Agents

Yang

Stolarzewicz

et al. 2023

Chem. Rev.

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The proportion of approved chiral drugs and drug candidates under medical studies has surged dramatically over the past two decades. As a consequence, the efficient synthesis of enantiopure pharmaceuticals or their synthetic intermediates poses a profound challenge to medicinal and process chemists. The significant advancement in asymmetric catalysis has provided an effective and reliable solution to this challenge. The successful application of transition metal catalysis, organocatalysis, and biocatalysis to the medicinal and pharmaceutical industries has promoted drug discovery by efficient and precise preparation of enantio-enriched therapeutic agents, and facilitated the industrial production of active pharmaceutical ingredient in an economic and environmentally friendly fashion. The present review summarizes the most recent applications (2008–2022) of asymmetric catalysis in the pharmaceutical industry ranging from process scales to pilot and industrial levels. It also showcases the latest achievements and trends in the asymmetric synthesis of therapeutic agents with state of the art technologies of asymmetric catalysis.

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Section: Biocatalysismentioning

confidence: 99%

Section: Oxidoreductasesmentioning

confidence: 99%

Enantioselective Transformations in the Synthesis of Therapeutic Agents

Yang

Stolarzewicz

et al. 2023

Chem. Rev.

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“…9 In this context, an arsenal of enzymes from different origins is now available for the synthesis of fluoroalkyl secondary alcohols with high optical purity, including PpKR8 from Paraburkholderia phymatum , 10 CaADH from Clostridium acetobutylicum , 11 Ras-ADH from Ralstonia sp., 12 KR01 from Leifsonia sp. S749, 13 PFADH from the hyperthermophilic archaeon Pyrococcus furiosus , 14 TtADH from Thermus thermophilus , 15 SsCR from S. salmonicolor , 16 KmCR2 from K. marxianus CBS4857, 17 etc . However, most of the developed biocatalytic methods focus on the asymmetric reduction of trifluoromethyl ketones, and the biocatalytic enantioselective reduction of difluoromethylene (CF 2 ) group-containing ketones remains less explored.…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic asymmetric reduction of fluoroalkyl ketones to access enantiopure fluoroalkyl secondary alcohols

Wang

et al. 2023

Org. Biomol. Chem.

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“…CA49 (Liu et al, 2014), Burkholderia cenocepacia (Yu et al, 2018), Leifsonia sp. S749 (Tang et al, 2019), and immobilized ketoreductase (Li et al, 2015). Some microorganisms or isolated enzymes have also been reported for their ability to produce (S)-[3,5-bis(trifluoromethyl)phenyl] ethanol ((S)-BTPE) from BTAP, such as Geotrichum candidum 90685 (Homann et al, 2004), Candida tropicalis 104 (Wang et al, 2011), Saccharomyces rhodotorula (Zhang et al, 2011), alcohol dehydrogenase from Rhodococcus erythropolis (Pollard et al, 2006), and engineered Escherichia coli (Dascier et al, 2014).…”

Section: Introductionmentioning

confidence: 99%