Asymmetric Ketone Reduction by Immobilized Rhodotorula mucilaginosa

Liu, Hui; Duan, Wendi; Souza, Fayene Zeferino Ribeiro de; Liu, Lan; Chen, Bi‐Shuang

doi:10.3390/catal8040165

Cited by 13 publications

(9 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The described storage conditions enabled the retention of 80% activity after about 10 months. High-throughput screening performed by Liu et al [36] revealed Rhodotorula mucilaginosa as a very active and selective whole-cell biocatalyst for the asymmetric reduction of various aromatic ketones to the desired chiral alcohols. For cell immobilization, agar, calcium alginate, PVA-alginate, and chitosan were employed as support matrices; pH tolerance and thermal stability were improved.…”

Section: This Special Issuementioning

confidence: 99%

Immobilized Biocatalysts

Grünwald

2018

Catalysts

View full text Add to dashboard Cite

show abstract

Section: This Special Issuementioning

confidence: 99%

Immobilized Biocatalysts

Grünwald

2018

Catalysts

View full text Add to dashboard Cite

show abstract

“…Enantiopure secondary alcohols are valuable and versatile precursors for the production of chiral drugs . Benzofurans with numerous application areas are bicyclic ring structures .…”

Section: Introductionmentioning

confidence: 99%

Green synthesis of enantiopure (S)‐1‐(benzofuran‐2‐yl)ethanol by whole‐cell biocatalyst

Şahin

2019

Chirality

View full text Add to dashboard Cite

Optically active aromatic alcohols are valuable chiral building blocks of many natural products and chiral drugs. Lactobacillus paracasei BD87E6, which was isolated from a cereal-based fermented beverage, was shown as a biocatalyst for the bioreduction of 1-(benzofuran-2-yl) ethanone to (S)-1-(benzofuran-2-yl) ethanol with highly stereoselectivity. The bioreduction conditions were optimized using L. paracasei BD87E6 to obtain high enantiomeric excess (ee) and conversion. After optimization of the bioreduction conditions, it was shown that the bioreduction of 1-(benzofuran-2-yl)ethanone was performed in mild reaction conditions. The asymmetric bioreduction of the 1-(benzofuran-2-yl)ethanone had reached 92% yield with ee of higher than 99.9% at 6.73 g of substrate. Our study gave the first example for enantiopure production of (S)-1-(benzofuran-2-yl)ethanol by a biological green method.This process is also scalable and has potential in application. In this study, a basic and novel whole-cell mediated biocatalytic method was performed for the enantiopure production of (S)-1-(benzofuran-2-yl)ethanol in the aqueous medium, which empowered the synthesis of a precious chiral intermediary process to be converted into a sophisticated molecule for drug production. KEYWORDS (S)-1-(benzofuran-2-yl)ethanol, asymmetric bioreduction, chirality, Lactobacillus paracasei BD87E6, whole-cell biocatalysts

show abstract

“…Enantiopure alcohols are valuable and versatile building blocks for the manufacturing of chiral pharmaceuticals [1]. (R)-1- phenyl]ethanol is a crucial enantiomerically enriched intermediate for the production of AD101 (SCH-350581), a chemokine CCR5 antagonist widely used in AIDS patients to inhibit the replication of HIV-1 via blockade of its entry into cells [2].…”

Section: Introductionmentioning

confidence: 99%

Efficient Biocatalytic Preparation of Optically Pure (R)-1-[4-(Trifluoromethyl)phenyl]ethanol by Recombinant Whole-Cell-Mediated Reduction

Chen¹,

Xia²,

Liu³

et al. 2019

Catalysts

View full text Add to dashboard Cite

(R)-1-[4-(Trifluoromethyl)phenyl]ethanol is an important pharmaceutical intermediate of a chemokine CCR5 antagonist. In the present study, a bioprocess for the asymmetric reduction of 4-(trifluoromethyl)acetophenone to (R)-1-[4-(trifluoromethyl)phenyl]ethanol was developed by recombinant Escherichia coli cells with excellent enantioselectivity. In order to overcome the conversion limitation performed in the conventional buffer medium resulting from poor solubility of non-natural substrate, we subsequently established a polar organic solvent-aqueous medium to improve the efficacy. Isopropanol was selected as the most suitable cosolvent candidate, based on the investigation on a substrate solubility test and cell membrane permeability assay in different organic solvent-buffer media. Under the optimum conditions, the preparative-scale asymmetric reduction generated a 99.1% yield with >99.9% product enantiomeric excess (ee) in a 15% (v/v) isopropanol proportion, at 100 mM of 4-(trifluoromethyl)acetophenone within 3 h. Compared to bioconversion in the buffer medium, the developed isopropanol-aqueous system enhanced the substrate concentration by 2-fold with a remarkably improved yield (from 62.5% to 99.1%), and shortened the reaction time by 21 h. Our study gave the first example for a highly enantioselective production of (R)-1-[4-(trifluoromethyl)phenyl]ethanol by a biological method, and the bioreduction of 4-(trifluoromethyl)acetophenone in a polar organic solvent-aqueous system was more efficient than that in the buffer solution only. This process is also scalable and has potential in application.

show abstract

Asymmetric Ketone Reduction by Immobilized Rhodotorula mucilaginosa

Cited by 13 publications

References 28 publications

Immobilized Biocatalysts

Immobilized Biocatalysts

Green synthesis of enantiopure (S)‐1‐(benzofuran‐2‐yl)ethanol by whole‐cell biocatalyst

Efficient Biocatalytic Preparation of Optically Pure (R)-1-[4-(Trifluoromethyl)phenyl]ethanol by Recombinant Whole-Cell-Mediated Reduction

Contact Info

Product

Resources

About