Enhancing asymmetric reduction of 3-chloropropiophenone with immobilized acetobacter sp. CCTCC M209061 cells by using deep eutectic solvents as cosolvents

ACS Sustainable Chemistry and Engineering

Volumn 3, Issue 4, 2015, Pages 718-724

  Xu, Pei ^a   Xu, Yu ^a   Li, Xiao Feng ^a   Zhao, Bing Yi ^a   Zong, Min Hua ^a   Lou, Wen Yong ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

3 chloropropiophenone; Biocatalysis; deep eutectic solvent; immobilized Acetobacter sp. CCTCC M209061; reduction; sustainable chemistry

Indexed keywords

ACETOBACTER; BIOCOMPATIBILITY; CATALYSIS; CELLS; CHLORINE COMPOUNDS; EUTECTICS; IONIC LIQUIDS; PRODUCTIVITY; REDUCTION; SODIUM SULFATE; SOLVENTS; SULFUR COMPOUNDS;

3-CHLOROPROPIOPHENONE; BIOCATALYSIS; DEEP EUTECTIC SOLVENTS; IMMOBILIZED ACETOBACTER SP. CCTCC M209061; SUSTAINABLE CHEMISTRY;

CYTOLOGY;

EID: 84926429773     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.5b00025     Document Type: Article

References (33)

1. Armstrong, A.; Carbery, D. R. Synthetic methods: Part (ii) Oxidation and reduction methods Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2006, 102, 34-49
2. Gamenara, D.; Domínguez de María, P. Candida spp. redox machineries: An ample biocatalytic platform for practical applications and academic insights Biotechnol. Adv. 2009, 27 (3) 278-285
3. James, W. H.; Lu, Z. H.; Jurgens, A. R.; Fang, Q. K.; Byers, P.; Stephen, A. W.; Senanayake, C. H. A practical asymmetric synthesis of (R)-fluoxetine and its major metabolite (R)-norfluoxetine Tetrahedron Lett. 2001, 42, 8919-8921
4. Schneider, M. P.; Goergens, U. An efficient route to enantiomerically pure antidepressants: Tomoxetine, nisoxetine and fluoxetine Tetrahedron: Asymmetry 1992, 3 (4) 525-528
5. Tian, J.; Guo, Q.; Chen, Y.; Li, X.; Shi, H.; Chen, L. Study on industrial metabolism of carbon in a Chinese fine chemical industrial park Environ. Sci. Technol. 2013, 47 (2) 1048-1056
6. Kroutil, W.; Mang, H.; Edegger, K.; Faber, K. Recent advances in the biocatalytic reduction of ketones and oxidation of sec-alcohols Curr. Opin. Chem. Biol. 2004, 8 (2) 120-126
7. Sanjay, G.; Sugunan, S. Enhanced pH and thermal stabilities of invertase immobilized on montmorillonite K-10 Food Chem. 2006, 94 (4) 573-579
8. Janeczko, T.; Kostrzewa-Susłow, E. Enantioselective reduction of propiophenone formed from 3-chloropropiophenone and stereoinversion of the resulting alcohols in selected yeast cultures Tetrahedron: Asymmetry 2014, 25 (18-19) 1264-1269
9. Yang, G. S.; Xu, J. Y.; Ou, Z. M.; Yao, S. J. Asymmetric reduction of (S)-3-chloro-1-phenylpropanol from 3-chloropropiophenone by preheated immobilized Candida utilis Biotechnol. Lett. 2009, 31 (12) 1879-1883
10. Yang, G. S.; Ou, Z. M.; Yao, S. J.; Xu, J. Y. Asymmetric reduction of 3-chloropropiophenone to (S)-3-chloro-1-phenylpropanol using immobilized Saccharomyces cerevisiae CGMCC 2266 cells J. Mol. Catal. B: Enzym. 2009, 57 (1-4) 83-88
11. Xiao, Z. J.; Zong, M. H.; Lou, W. Y. 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) 5560-5565
12. Abbott, A. P.; Boothby, D.; Capper, G.; Davies, D. L.; Rasheed, R. K. Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids J. Am. Chem. Soc. 2004, 126, 9142-9147
13. Paiva, A.; Craveiro, R.; Aroso, I.; Martins, M.; Reis, R. L.; Duarte, A. R. C. Natural deep eutectic solvents-Solvents for the 21st century ACS Sustainable Chem. Eng. 2014, 2 (5) 1063-1071
14. Zhang, Q. H.; De Oliveira Vigier, K.; Royer, S.; Jerome, F. Deep eutectic solvents: Syntheses, properties and applications Chem. Soc. Rev. 2012, 41 (21) 7108-7146
15. Hayyan, M.; Hashim, M. A.; Hayyan, A.; Al-Saadi, M. A.; AlNashef, I. M.; Mirghani, M. E. S.; Saheed, O. K. Are deep eutectic solvents benign or toxic? Chemosphere 2013, 90 (7) 2193-2195
16. Domínguez de María, P.; Maugeri, Z. Ionic liquids in biotransformations: from proof-of-concept to emerging deep-eutectic-solvents Curr. Opin. Chem. Biol. 2011, 15 (2) 220-225
17. Zhao, H.; Baker, G. A.; Holmes, S. Protease activation in glycerol-based deep eutectic solvents J. Mol. Catal. B: Enzym. 2011, 72 (3-4) 163-167
18. Lindberg, D.; de la Fuente Revenga, M.; Widersten, M. Deep eutectic solvents (DESs) are viable cosolvents for enzyme-catalyzed epoxide hydrolysis J. Biotechnol. 2010, 147 (3-4) 169-171
19. Gorke, J. T.; Srienc, F.; Kazlauskas, R. J. Hydrolase-catalyzed biotransformations in deep eutectic solvents Chem. Commun. 2008, 10, 1235-1237
20. Maugeri, Z.; Domínguez de María, P. Whole-cell biocatalysis in deep-eutectic-solvents/aqueous mixtures ChemCatChem. 2014, 6 (6) 1535-1537
21. Chen, X. H.; Lou, W. Y.; Zong, M. H.; Smith, T. J. Optimization of culture conditions to produce high yields of active Acetobacter sp. CCTCC M209061 cells for anti-prelog reduction of prochiral ketones BMC biotechnology 2011, 11, 110
22. Quezada, M. A.; Carballeira, J. D.; Sinisterra, J. V. Monascus kaoliang CBS 302.78 immobilized in polyurethane foam using iso-propanol as co-substrate: Optimized immobilization conditions of a fungus as biocatalyst for the reduction of ketones Bioresour. Technol. 2009, 100 (6) 2018-2025
23. Wolfson, A.; Dlugy, C.; Tavor, D.; Blumenfeld, J.; Shotland, Y. Bakers yeast catalyzed asymmetric reduction in glycerol Tetrahedron: Asymmetry 2006, 17 (14) 2043-2045
24. Gangu, S. A.; Weatherley, L. R.; Scurto, A. M. Whole-cell biocatalysis with ionic liquids Curr. Org. Chem. 2009, 13 (13) 1242-1258
25. Hoefel, D.; Grooby, W. L.; Monis, P. T.; Andrews, S.; Saint, C. P. Enumeration of water-borne bacteria using viability assays and flow cytometry: A comparison to culture-based techniques J. Microbiol. Methods 2003, 55 (3) 585-597
26. Lou, W. Y.; Wang, W.; Li, R. F.; Zong, M. H. 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) 190-197
27. Lou, W. Y.; Zong, M. H.; Smith, T. J. Use of ionic liquids to improve whole-cell biocatalytic asymmetric reduction of acetyltrimethylsilane for efficient synthesis of enantiopure (S)-1-trimethylsilylethanol Green Chem. 2006, 8 (2) 147-155
28. Shen, D.; Xu, J. H.; Wu, H. Y.; Liu, Y. Y. Significantly improved esterase activity of Trichosporon brassicae cells for ketoprofen resolution by 2-propanol treatment J. Mol. Catal. B: Enzym. 2002, 18, 219-224
29. Wang, X. T.; Chen, X. H.; Xu, Y.; Lou, W. Y.; Wu, H.; Zong, M. H. Biocatalytic anti-Prelog stereoselective reduction of ethyl acetoacetate catalyzed by whole cells of Acetobacter sp. CCTCC M209061 J. Biotechnol. 2013, 163, 292-300
30. Coronel, C.; Arce, G.; Iglesias, C.; Noguera, C. M.; Bonnecarrère, P. R.; Giordano, S. R.; Gonzalez, D. Chemoenzymatic synthesis of fluoxetine precursors. Reduction of β-substituted propiophenones J. Mol. Catal. B: Enzym. 2014, 102, 94-98
31. Yu, C. Y.; Wei, P.; Li, X. F.; Zong, M. H.; Lou, W. Y. Using ionic liquid in a biphasic system to improve asymmetric hydrolysis of styrene oxide catalyzed by cross-linked enzyme aggregates (CLEAs) of mung bean epoxide hydrolases Ind. Eng. Chem. Res. 2014, 53 (19) 7923-7930
32. Wang, W.; Zong, M. H.; Lou, W. Y. Use of an ionic liquid to improve asymmetric reduction of 4-methoxyacetophenone catalyzed by immobilized Rhodotorula sp. AS2.2241 cells J. Mol. Catal. B: Enzym. 2009, 56 (1) 70-76
33. Pfruender, H.; Amidjojo, M.; Kragl, U.; Weuster-Botz, D. Efficient whole-cell biotransformation in a biphasic ionic liquid/water system Angew. Chem., Int. Ed. 2004, 43 (34) 4529-4531