Response surface methodology as optimization strategy for asymmetric bioreduction of acetophenone using whole cell of Lactobacillus senmaizukei

References

• Breuer, M.; Ditrich, K.; Habicher, T.; Hauer, B.; Keßeler, M.; Stürmer, R.; Zelinski, T. Industrial Methods for the Production of Optically Active Intermediates. Angew. Chem. Int. Ed. 2004, 43, 788–824. DOI: 10.1002/anie.200300599.
   PubMed Web of Science ®Google Scholar
• Gladiali, S.; Alberico, E. Asymmetric Transfer Hydrogenation: Chiral Ligands and Applications. Chem. Soc. Rev. 2006, 35, 226–236. DOI: 10.1039/B513396C.
   PubMed Web of Science ®Google Scholar
• Ikariya, T.; Blacker, A.J. Asymmetric Transfer Hydrogenation of Ketones with Bifunctional Transition Metal-Based Molecular. Acc. Chem. Res. 2007, 40, 1300–1308. DOI: 10.1021/ar700134q.
   PubMed Web of Science ®Google Scholar
• Ikariya, T.; Murata, K.; Noyori, R. Bifunctional Transition Metal-Based Molecular Catalysts for Asymmetric Syntheses. Org. Biomol. Chem. 2006, 4, 393–406. DOI: 10.1039/B513564H.
   PubMed Web of Science ®Google Scholar
• Wu, X.F.; Xiao, J.L. Aqueous-Phase Asymmetric Transfer Hydrogenation of Ketones-a Greener Approach to Chiral Alcohols. Chem. Commun. 2007, 24, 2449–2466. DOI: 10.1039/b618340a.
   Google Scholar
• Kamal, A.; Khanna, G.R.; Ramu, R.; Krishnaji, T. Chemoenzymatic Synthesis of Duloxetine and Its Enantiomer: Lipase-Catalyzed Resolution of 3-Hydroxy-3-(2-Thienyl) Propanenitrile. Tetrahedron Lett. 2003, 44, 4783–4787. DOI: 10.1016/S0040-4039(03)00945-6.
   Web of Science ®Google Scholar
• More, G.V.; Badgujar, K.C.; Bhanage, B.M. Kinetic Resolution of Secondary Alcohols with Burkholderia cepacia Lipase Immobilized on a Biodegradable Ternary Blend Polymer Matrix as a Highly Efficient and Heterogeneous Recyclable Biocatalyst. RSC Adv. 2015, 5, 4592–4598. DOI: 10.1039/C4RA14478C.
   Web of Science ®Google Scholar
• Sukhorukov, A.Y.; Sukhanova, A.A.; Zlotin, S.G. Stereoselective Reactions of Nitro Compounds in the Synthesis of Natural Compound Analogs and Active Pharmaceutical Ingredients. Tetrahedron 2016, 72, 6191–6281. DOI: 10.1016/j.tet.2016.07.067.
   Web of Science ®Google Scholar
• Comasseto, J.V.; Andrade, L.H.; Omori, A.T.; Assis, L.F.; Porto, A.L.M. Deracernization of Aryl Ethanols and Reduction of Acetophenones by Whole Fungal Cells of Aspergillus terreus CCT 4083, A. terreus CCT 3320 and Rhizopus oryzae CCT 4964. J. Mol. Catal. B. Enzym. 2004, 29, 55–61. DOI: 10.1016/j.molcatb.2004.01.015.
   Google Scholar
• Patel, R.N.; Goswami, A.; Chu, L.; Donovan, M.J.; Nanduri, V.; Goldberg, S.; Johnston, R.; Siva, P.J.; Nielsen, B.; Fan, J.; et al. Enantioselective Microbial Reduction of Substituted Acetophenones. Tetrahedron: Asymmetry 2004, 15, 1247–1258. DOI: 10.1016/j.tetasy.2004.02.024.
   Web of Science ®Google Scholar
• Murzin, D.Y.; Maki-Arvela, P.; Toukoniitty, E.; Salmi, T. Asymmetric Heterogeneous Catalysis: Science and Engineering. Catal. Rev. 2005, 47, 175–256. DOI: 10.1081/CR-200057461.
   Web of Science ®Google Scholar
• Pollard, D.J.; Woodley, J.M. Biocatalysis for Pharmaceutical Intermediates: The Future Is Now. Trends Biotechnol. 2007, 25, 66–73. DOI: 10.1016/j.tibtech.2006.12.005.
   PubMed Web of Science ®Google Scholar
• Soyer, A.; Bayraktar, E.; Mehmetoglu, Ü. Optimization of Lipase-Catalyzed Enantioselective Production of 1-Phenyl 1-Propanol Using Response Surface Methodology. Prep. Biochem. Biotechnol. 2010, 40, 389–404. DOI: 10.1080/10826068.2010.525433.
   PubMed Web of Science ®Google Scholar
• Yuan, R.; Watanabe, S.; Kuwabata, S.; Yoneyama, H. Asymmetric Electroreduction of Ketone and Aldehyde Derivatives to the Corresponding Alcohols Using Alcohol Dehydrogenase as an Electrocatalyst. J. Org. Chem. 1997, 62, 2494–2499. DOI: 10.1021/jo9620573.
   PubMed Web of Science ®Google Scholar
• Yun, H.; Yang, Y.H.; Cho, B.K.; Hwang, B.Y.; Kim, B.G. Simultaneous Synthesis of Nantiomerically Pure (R)-1-Phenylethanol and (R)-Alpha-Methylbenzylamine from Racemic Alpha-Methylbenzylamine Using Omegatransaminase/Alcohol Dehydrogenase/Glucose Dehydrogenase Coupling Reaction. Biotechnol. Lett. 2003, 25, 809–814.
   PubMed Web of Science ®Google Scholar
• Ferloni, C.; Heinemann, M.; Hummel, W.; Daussmann, T.; Buchs, J. Optimization of Enzymatic Gas-Phase Reactions by Increasing the Long-Term Stability of the Catalyst. Biotechnol. Prog. 2004, 20, 975–978. DOI: 10.1021/bp034334e.
   PubMed Web of Science ®Google Scholar
• De Temino, D.M.; Hartmeier, W.; Ansorge-Schumacher, M.B. Entrapment of the Alcohol Dehydrogenase from Lactobacillus kefir in Polyvinyl Alcohol for the Synthesis of Chiral Hydrophobic Alcohols in Organic Solvents. Enzyme. Microb. Technol. 2005, 36, 3–9. DOI: 10.1016/j.enzmictec.2004.01.013.
   Web of Science ®Google Scholar
• Gao, K.; Song, Q.; Wei, D. Coupling of Enantioselective Biooxidation of DL-1,2-Propanediol and Bioreduction of Pinacolone via Regeneration Cycle of Coenzyme. Appl. Microbiol. Biotechnol. 2006, 41, 819–823. DOI: 10.1007/s00253-005-0231-3.
   Google Scholar
• Pereira, R.S. The Use of Baker's Yeast in the Generation of Asymmetric Centers to Produce Chiral Drugs and Others Compounds. Crit. Rev. Biotechnol. 1998, 18, 25–64. DOI: 10.1080/0738-859891224211.
   PubMed Web of Science ®Google Scholar
• Braiuca, P.; Ebert, C.; Basso, A.; Linda, P.; Gardossi, L. Computational Methods to Rationalize Experimental Strategies in Biocatalysis. Trends Biotechnol. 2006, 24, 419–425. DOI: 10.1016/j.tibtech.2006.07.001.
   PubMed Web of Science ®Google Scholar
• Öksüz, S.; Şahin, E.; Dertli, E. Synthesis of Enantiomerically Enriched Drug Precursors by Lactobacillus paracasei BD 87E6 as a Biocatalyst. Chem. Biodivers. 2018, 15, e1800028. DOI: 10.1002/cbdv.201800028.
   PubMed Web of Science ®Google Scholar
• Karnopp, A.R.; Oliveira, K.G.; de Andrade, E.F.; Postingher, B.M.; Granato, D. Optimization of an Organic Yogurt Based on Sensorial, Nutritional, and Functional Perspectives. Food Chem. 2017, 233, 401–411. DOI: 10.1016/j.foodchem.2017.04.112.
   PubMed Web of Science ®Google Scholar
• Myers, R.H.; Montgomery, D.C. Response Surface Methodology. Willey Inter-Science, Hoboken, NY, 1995.
   Google Scholar
• Şahin, E. Production of (R)-1-(1,3-benzodioxol-5-yl)ethanol in High Enantiomeric Purity by Lactobacillus paracasei BD101. Chirality 2018, 30, 189–194. DOI: 10.1002/chir.22782.
   PubMed Web of Science ®Google Scholar
• Nakamura, K.; Yamanaka, R.; Matsuda, T.; Harada, T. Recent Developments in Asymmetric Reduction of Ketones with Biocatalysts. Tetrahedron Asymm. 2003, 14, 2659–2681. DOI: 10.1016/S0957-4166(03)00526-3.
   Web of Science ®Google Scholar
• Mandal, D.; Ahmad, A.; Khan, M.I.; Kumar, R. Enantioselective Bioreduction of Acetophenone and Its Analogous by the Fungus Trichothecium sp. J. Mol. Catal. B: Enzym. 2004, 27, 61–63. DOI: 10.1016/j.molcatb.2003.09.009.
   Web of Science ®Google Scholar
• Şahin, E. Debaryomyces hansenii as a New Biocatalyst in the Asymmetric Reduction of Substituted Acetophenones. Biocatal. Biotransform. 2017, 35, 363–371. DOI: 10.1080/10242422.2017.1348500.
   Web of Science ®Google Scholar
• Yılmaz, D.; Şahin, E.; Dertli, E. Highly Enantioselective Production of Chiral Secondary Alcohols Using Lactobacillus paracasei BD 101 as a New Whole Cell Biocatalyst and Evaluation of Their Antimicrobial Effects. Chem. Biodivers. 2017, 14, e1700269. DOI: 10.1002/cbdv.201700269.
   Web of Science ®Google Scholar
• Kurbanoglu, E.B.; Zilbeyaz, K.; Kurbanoglu, N.I.; Kilic, H. Enantioselective Reduction of Substituted Acetophenones by Aspergillus niger. Tetrahedron: Asymmetry 2007, 18, 1159–1162. DOI: 10.1016/j.tetasy.2007.05.017.
   Google Scholar
• Sohrabi, S.; Akhlaghian, F. Modeling and Optimization of Phenol Degradation over Copper-Doped Titanium Dioxide Photocatalyst Using Response Surface Methodology. Process. Saf. Environ. Prot. 2016, 99, 120–128. DOI: 10.1016/j.psep.2015.10.016.
   Web of Science ®Google Scholar
• Sohrabi, S.; Akhlaghian, F. Surface Investigation and Catalytic Activity of Iron-Modified TiO2. J. Nanostruct. Chem. 2016, 6, 93–102.
   Web of Science ®Google Scholar
• Prelog, V. Specification of the Stereospecificity of Some Oxido-Reductases by Diamond Lattice Sections. Pure Appl. Chem. 1964, 9, 119–130. DOI: 10.1351/pac196409010119.
   Google Scholar