New Anti-Prelog Stereospecific Whole-Cell Biocatalyst for Asymmetric Reduction of Prochiral Ketones

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2023 Feb 11

PMID 36771091

Authors

Min-Yu Wang

Shun-Ju Cai

Jia-Chun Lin

Xiao-Jun Ji

Zhi-Gang Zhang

Affiliations

Soon will be listed here.

Abstract

The biocatalytic asymmetric reduction of prochiral ketones for the production of enantiopure alcohols is highly desirable due to its inherent advantages over chemical methods. In this study, a new bacterial strain capable of transforming ketones to corresponding alcohols with high activity and excellent enantioselectivity was discovered in a soil sample. The strain was subsequently identified as TQ-2 based on its physiological characteristics and 16S rDNA sequence analysis. Under optimized reaction conditions, the resting cells of TQ-2 converted acetophenone to enantioenriched ()-1-phenylethanol with 99% enantiometric excess following anti-Prelog's rule, which is scarce in biocatalytic ketone reduction. The optimum temperature for the cells was 30 °C, and considerable catalytic activity was observed over a broad pH range from 5.0 to 9.0. The cells showed enhanced catalytic activity in the presence of 15% () glycerol as a co-substrate. The catalytic activity can also be substantially improved by adding Ca or K ions. Moreover, the TQ-2 cell was highly active in reducing several structurally diverse ketones and aldehydes to form corresponding alcohols with good to excellent conversion. Our study provides a versatile whole-cell biocatalyst that can be used in the asymmetric reduction of ketones for the production of chiral alcohol, thereby expanding the biocatalytic toolbox for potential practical applications.

References

Lou W, Wang W, Li R, Zong M . Efficient enantioselective reduction of 4'-methoxyacetophenone with immobilized Rhodotorula sp. AS2.2241 cells in a hydrophilic ionic liquid-containing co-solvent system. J Biotechnol. 2009; 143(3):190-7. DOI: 10.1016/j.jbiotec.2009.07.004. View

Hollmann F, Opperman D, Paul C . Biocatalytic Reduction Reactions from a Chemist's Perspective. Angew Chem Int Ed Engl. 2020; 60(11):5644-5665. PMC: 7983917. DOI: 10.1002/anie.202001876. View

Koesoema A, Standley D, Senda T, Matsuda T . Impact and relevance of alcohol dehydrogenase enantioselectivities on biotechnological applications. Appl Microbiol Biotechnol. 2020; 104(7):2897-2909. DOI: 10.1007/s00253-020-10440-2. View

Goldberg K, Schroer K, Lutz S, Liese A . Biocatalytic ketone reduction--a powerful tool for the production of chiral alcohols-part II: whole-cell reductions. Appl Microbiol Biotechnol. 2007; 76(2):249-55. DOI: 10.1007/s00253-007-1005-x. View

Zheng G, Xu J . New opportunities for biocatalysis: driving the synthesis of chiral chemicals. Curr Opin Biotechnol. 2011; 22(6):784-92. DOI: 10.1016/j.copbio.2011.07.002. View

Huisman G, Liang J, Krebber A . Practical chiral alcohol manufacture using ketoreductases. Curr Opin Chem Biol. 2010; 14(2):122-9. DOI: 10.1016/j.cbpa.2009.12.003. View

Mordhorst S, Andexer J . Round, round we go - strategies for enzymatic cofactor regeneration. Nat Prod Rep. 2020; 37(10):1316-1333. DOI: 10.1039/d0np00004c. View

Patel R . Biocatalysis for synthesis of pharmaceuticals. Bioorg Med Chem. 2017; 26(7):1252-1274. DOI: 10.1016/j.bmc.2017.05.023. View

Zhang Y, Zhang H, Cheng F, Xia Y, Zheng J, Wang Z . Whole-cell biocatalytic of Bacillus cereus WZZ006 strain to synthesis of indoxacarb intermediate: (S)-5-Chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester. Chirality. 2019; 31(11):958-967. DOI: 10.1002/chir.23124. View

10.

You Z, Liu Z, Zheng Y . Chemical and enzymatic approaches to the synthesis of optically pure ethyl (R)-4-cyano-3-hydroxybutanoate. Appl Microbiol Biotechnol. 2013; 98(1):11-21. DOI: 10.1007/s00253-013-5357-0. View

11.

Li J, Wang P, He J, Huang J, Tang J . Efficient biocatalytic synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol by a newly isolated Trichoderma asperellum ZJPH0810 using dual cosubstrate: ethanol and glycerol. Appl Microbiol Biotechnol. 2013; 97(15):6685-92. DOI: 10.1007/s00253-013-4973-z. View

12.

Reetz M . Biocatalysis in organic chemistry and biotechnology: past, present, and future. J Am Chem Soc. 2013; 135(34):12480-96. DOI: 10.1021/ja405051f. View

13.

Tang D, Liu W, Huang L, Cheng L, Xu Z . Efficient biotransformation of vitamin D to 25-hydroxyvitamin D by a newly isolated Bacillus cereus strain. Appl Microbiol Biotechnol. 2019; 104(2):765-774. DOI: 10.1007/s00253-019-10250-1. View

14.

Hu J, Xu Y . Anti-prelog reduction of prochiral carbonyl compounds by Oenococcus oeni in a biphasic system. Biotechnol Lett. 2006; 28(14):1115-9. DOI: 10.1007/s10529-006-9062-2. View

15.

An J, Nie Y, Xu Y . Structural insights into alcohol dehydrogenases catalyzing asymmetric reductions. Crit Rev Biotechnol. 2019; 39(3):366-379. DOI: 10.1080/07388551.2019.1566205. View

16.

Kisukuri C, Andrade L . Production of chiral compounds using immobilized cells as a source of biocatalysts. Org Biomol Chem. 2015; 13(40):10086-107. DOI: 10.1039/c5ob01677k. View

17.

Banerjee A, Ghoshal A . Phenol degradation by Bacillus cereus: pathway and kinetic modeling. Bioresour Technol. 2010; 101(14):5501-7. DOI: 10.1016/j.biortech.2010.02.018. View

18.

Seliger J, Oestreich M . Making the Silylation of Alcohols Chiral: Asymmetric Protection of Hydroxy Groups. Chemistry. 2019; 25(40):9358-9365. DOI: 10.1002/chem.201900792. View

19.

Xiao Z, Zong M, Lou W . Highly enantioselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to enantiopure (R)-4-(trimethylsilyl)-3-butyn-2-ol using a novel strain Acetobacter sp. CCTCC M209061. Bioresour Technol. 2009; 100(23):5560-5. DOI: 10.1016/j.biortech.2009.06.006. View

20.

de Carvalho C . Whole cell biocatalysts: essential workers from Nature to the industry. Microb Biotechnol. 2016; 10(2):250-263. PMC: 5328830. DOI: 10.1111/1751-7915.12363. View