Efficient biosynthesis of enantiopure tolvaptan by utilizing alcohol dehydrogenase-catalyzed enantioselective reduction

Zhang, Honglei; Zhang, Chao; Han, Mengnan; Pei, C.-H.; Xu, Zhidong; Li, Wei

doi:10.1039/c7gc03679e

Cited by 8 publications

(3 citation statements)

References 14 publications

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“…The recombinant protein CpFDH from Candida parapsilosis C5 was purified by a purifier system (ÄKTA pure; GE Healthcare) with an affinity column filled with precharged Ni Sepharose™ (HisTrap HP; GE Healthcare, Piscataway, NJ, USA; Fig. S6) in our previous study (Zhang et al ., 2018). The activity of CpFDH was assayed by measuring the increase in absorbance at 340 nm.…”

Section: Methodsmentioning

confidence: 99%

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

Han

Wang

Pei

et al. 2020

Microbial Biotechnology

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Summary Chiral aromatic alcohols have received much attention due to their widespread use in pharmaceutical industries. In the asymmetric synthesis processes, the excellent performance of alcohol dehydrogenase makes it a good choice for biocatalysts. In this study, a novel and robust medium‐chain alcohol dehydrogenase RhADH from Rhodococcus R6 was discovered and used to catalyse the asymmetric reduction of aromatic ketones to chiral aromatic alcohols. The reduction of 2‐hydroxyacetophenone (2‐HAP) to (R)‐(‐)‐1‐phenyl‐1,2‐ethanediol ((R)‐PED) was chosen as a template to evaluate its catalytic activity. A specific activity of 110 U mg−1 and a 99% purity of e.e. was achieved in the presence of NADH. An efficient bienzyme‐coupled catalytic system (RhADH and formate dehydrogenase, CpFDH) was established using a two‐phase strategy (dibutyl phthalate and buffer), which highly raised the tolerated substrate concentration (60 g l−1). Besides, a broad range of aromatic ketones were enantioselectively reduced to the corresponding chiral alcohols by this enzyme system with highly enantioselectivity. This system is of the potential to be applied at a commercial scale.

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Section: Methodsmentioning

confidence: 99%

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

Han

Wang

Pei

et al. 2020

Microbial Biotechnology

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“…Biocatalysts are increasingly used as efficient and environmentally safe alternatives than traditional catalysts in the production of fine chemicals, difficult to make using conventional organic catalysts. 4,[16][17][18][19] Mohammadi et al found that (S)-1-tetralol (S)-2 was obtained in 75% yield and 91% enantiomeric excess (ee) using Brassica oleracea whole-cell biocatalyst. 20 Similarly, Yadav et al reported that Daucus carota exhibited good performance in the asymmetric reduction of 1 to (S)-2 in terms of enantioselectivity (96% ee), but low conversion (70%) and yield (52%).…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, there is an important to conduct studies about asymmetric reduction of 1 using biocatalysts. Biocatalysts are increasingly used as efficient and environmentally safe alternatives than traditional catalysts in the production of fine chemicals, difficult to make using conventional organic catalysts 4,16–19 . Mohammadi et al found that ( S )‐1‐tetralol ( S )‐2 was obtained in 75% yield and 91% enantiomeric excess (ee) using Brassica oleracea whole‐cell biocatalyst 20 .…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic asymmetric synthesis of (R)‐1‐tetralol using Lactobacillus paracasei BD101

Kalay

Şahin

2021

Chirality

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Asymmetric bioreduction of ketones is a fundamental process in the production of organic molecules. Compounds containing tetralone rings are found in the structure of many biologically active and pharmaceutical molecules. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of Lactobacillus paracasei BD101 was investigated as whole-cell biocatalyst in the enantioselective reduction of 1-tetralone (1). In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. (R)-1-tetralol ((R)-2), which can be used to treat disorder such as obsessive compulsive, posttraumatic stress, premenstrual dysphoric, and social anxiety, was manufactured in enantiopure form, high yield and gram-scale, using whole-cell biocatalysts of L. paracasei BD101. The 7.04 g of (R)-2 was obtained in optically pure form with 95% yield. Also, to our knowledge, this is the first report on production of (R)-2 using whole-cell biocatalyst in excellent yield, conversion, enantiopure form and gram scale. This is a clean, eco-friendly and cheap method for the synthesis of (R)-2 compared with chemical catalyst.

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Characterization and Application of a Novel Glucose Dehydrogenase with Excellent Organic Solvent Tolerance for Cofactor Regeneration in Carbonyl Reduction

Jiang

et al. 2023

Appl Biochem Biotechnol

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Efficient biosynthesis of enantiopure tolvaptan by utilizing alcohol dehydrogenase-catalyzed enantioselective reduction

Abstract: Using whole cells of Escherichia coli co-expressing alcohol dehydrogenase (PsADH) and formate dehydrogenase (CpFDH) in a biphasic aqueous–soybean oil system is shown to be an efficient method for the biosynthesis of enantiopure tolvaptan.

Cited by 8 publications

References 14 publications

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

Biocatalytic asymmetric synthesis of (R)‐1‐tetralol using Lactobacillus paracasei BD101

Characterization and Application of a Novel Glucose Dehydrogenase with Excellent Organic Solvent Tolerance for Cofactor Regeneration in Carbonyl Reduction

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