Taguchi analysis and asymmetric keto-reduction of acetophenone and its derivatives by soil filamentous fungal isolate: Penicillium rubens VIT SS1

References

• Yılmaz, D.; Şahin, E.; Dertli, E. Highly Enantioselective Production of Chiral Secondary Alcohols Using Lactobacillus paracasei BD101 as a New Whole Cell Biocatalyst and Evaluation of Their Antimicrobial Effects. Chem. Biodiversity 2017, 14, e1700269. DOI: 10.1002/cbdv.201700269.
   Web of Science ®Google Scholar
• Highly Enantioselective Production of Chiral Secondary Alcohols with Candida zeylanoides as a New Whole Cell Biocatalyst, Şahin 2017, Chemistry & Biodiversity. Wiley Online Library. Available at: https://onlinelibrary.wiley.com/doi/abs/10.1002/cbdv.201700121 (accessed Jun 5, 2020).
   Google Scholar
• Şahin, E.; Serencam, H.; Dertli, E. Whole Cell Application of Lactobacillus paracasei BD101 to Produce Enantiomerically Pure (S)-Cyclohexyl(Phenyl)Methanol. Chirality 2019, 31, 211–218. DOI: 10.1002/chir.23048.
   PubMed Web of Science ®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
• Synthesis of Enantiomerically Enriched Drug Precursors by Lactobacillus paracasei BD87E6 as a Biocatalyst, Öksüz 2018. Chemistry & Biodiversity. Wiley Online Library. Available at: https://onlinelibrary.wiley.com/doi/abs/10.1002/cbdv.201800028. (accessed Jun 5, 2020).
   Google Scholar
• Borges, K. B.; Borges, W.; de S.; Durán-Patrón, R.; Pupo, M. T.; Bonato, P. S.; Collado, I. G. Stereoselective Biotransformations Using Fungi as Biocatalysts. Tetrahedron: Asymmetry 2009, 20, 385–397. DOI: 10.1016/j.tetasy.2009.02.009.
   Web of Science ®Google Scholar
• Kuncham, R.; Gurumurthy, K. T.; Chandan, N.; Javed, A.; Ashwini, L. S.; Shenoi, R.; Baranwal, A. Biocatalytic Ketone Reduction - A Study on Screening and Effect of Culture Conditions on the Reduction of Selected Ketones. ILNS. 2013, 6, 54–77. DOI: 10.18052/www.scipress.com/ILNS.6.54.
   Google Scholar
• Şahin, E. Green Synthesis of Enantiopure (S)-1-(Benzofuran-2-Yl)Ethanol by Whole-Cell Biocatalyst. Chirality 2019, 31, 892–897. DOI: 10.1002/chir.23123.
   PubMed Web of Science ®Google Scholar
• Tozlu, C.; Şahin, E.; Serencam, H.; Dertli, E. Production of Enantiomerically Enriched Chiral Carbinols Using Weissella Paramesenteroides as a Novel Whole Cell Biocatalyst. Biocatal. Biotransform. 2019, 37, 388–398. DOI: 10.1080/10242422.2019.1568416.
   Web of Science ®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
• Kurbanoglu, E. B.; Zilbeyaz, K.; Ozdal, M.; Taskin, M.; Kurbanoglu, N. I. Asymmetric Reduction of Substituted Acetophenones Using Once Immobilized Rhodotorula Glutinis Cells. Bioresour. Technol. 2010, 101, 3825–3829. DOI: 10.1016/j.biortech.2010.01.016.
   PubMed Web of Science ®Google Scholar
• Şahin, E.; Dertli, E.. Biocatalyzed Enantiomerically Pure Production of (S)‐Phenyl(thiophen‐2‐yl)methanol - Şahin 2019. J. Heterocycl. Chem. 2019, 56, 2884–2888.
   Web of Science ®Google Scholar
• Baydaş, Y.; Dertli, E.; Şahin, E. Green Synthesis of Chiral Aromatic Alcohols with Lactobacillus kefiri P2 as a Novel Biocatalyst. Synth. Commun. 2020, 50, 1035–1045. DOI: 10.1080/00397911.2020.1729809.
   Web of Science ®Google Scholar
• Şahin, E.; Serencam, H.; Dertli, E. Production of Enantiomerically Pure (S)-Phenyl(Pyridin-2-Yl)Methanol with Lactobacillus paracasei BD101. Biocatal. Biotransform. 2019, 37, 448–454. DOI: 10.1080/10242422.2019.1602611.
   Web of Science ®Google Scholar
• Rocha, L. C.; Ferreira, H. V.; Pimenta, E. F.; Berlinck, R. G. S.; Seleghim, M. H. R.; Javaroti, D. C. D.; Sette, L. D.; Bonugli, R. C.; Porto, A. L. M. Bioreduction of alpha-chloroacetophenone by whole cells of marine fungi. Biotechnol. Lett. 2009, 31, 1559–1563. DOI: 10.1007/s10529-009-0037-y.
   PubMed Web of Science ®Google Scholar
• Şahin, E. Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones: Biocatalysis and Biotransformation. Biocatal. Biotransfor. 35, 363–371.
   Web of Science ®Google Scholar
• Patel, R. N.; Goswami, A.; Chu, L.; Nanduri, V.; Goldberg, S.; Johnston, R.; Donovan, M. J. Stereoselective Reduction of Substituted Acetophenone, October 5, 2004.
   Google Scholar
• Xie, Q.; Wu, J.; Xu, G.; Yang, L. Asymmetric Reduction of O-Chloroacetophenone with Candida pseudotropicalis 104. Biotechnol. Prog. 2006, 22, 1301–1304. DOI: 10.1021/bp0600583.
   PubMed Web of Science ®Google Scholar
• Tokoshima, D.; Hanaya, K.; Shoji, M.; Sugai, T. Whole-Cell Yeast-Mediated Preparation of (R)-2-Chloro-1-(3-Nitrophenyl)Ethanol as a Synthetic Precursor for (R)-Phenylephrine. J. Mol. Catal. B: Enzym. 2013, 97, 95–99. DOI: 10.1016/j.molcatb.2013.07.021.
   Google Scholar
• Decarlini, M. F.; Aimar, M. L.; Vázquez, A. M.; Vero, S.; Rossi, L. I.; Yang, P. Fungi Isolated from Food Samples for an Efficient Stereoselective Production of Phenylethanols. Biocatal. Agric. Biotechnol. 2017, 12, 275–285. DOI: 10.1016/j.bcab.2017.10.014.
   Web of Science ®Google Scholar
• Peng, G.-J.; Kuan, Y.-C.; Chou, H.-Y.; Fu, T.-K.; Lin, J.-S.; Hsu, W.-H.; Yang, M.-T. Stereoselective Synthesis of (R)-Phenylephrine Using Recombinant Escherichia coli Cells Expressing a Novel Short-Chain Dehydrogenase/Reductase Gene from Serratia marcescens BCRC 10948. J. Biotechnol. 2014, 170, 6–9. DOI: 10.1016/j.jbiotec.2013.11.011.
   PubMed Web of Science ®Google Scholar
• Sethi, M. K.; Bhandya, S. R.; Maddur, N.; Shukla, R.; Kumar, A.; Jayalakshmi Mittapalli, V. S. N. Asymmetric Synthesis of an Enantiomerically Pure Rivastigmine Intermediate Using Ketoreductase. Tetrahedron: Asymmetry 2013, 24, 374–379. DOI: 10.1016/j.tetasy.2013.01.023.
   Google Scholar
• Toma, F.; Abdulla, N. Isolation, Identification and Seasonal Distribution of Soilborne Fungi in Different Areas of Erbil Governorate. JALRB 2012, 3, 246–255.
   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
• Wu, Y.; Guan, K.; Wang, Z.; Xu, B.; Zhao, F. Isolation, Identification and Characterization of an Electrogenic Microalgae Strain. PLoS One. 2013, 8, e73442. DOI: 10.1371/journal.pone.0073442.
   PubMed Web of Science ®Google Scholar
• Kurbanoglu, E. B.; Zilbeyaz, K.; Kurbanoglu, N. I. Cryptococcus Laurentii as a New Biocatalyst for the Asymmetric Reduction of Substituted Acetophenones. Tetrahedron: Asymmetry 2011, 22, 345–350. DOI: 10.1016/j.tetasy.2011.01.014.
   Google Scholar
• Perna, F. M.; Ricci, M. A.; Scilimati, A.; Mena, M. C.; Pisano, I.; Palmieri, L.; Agrimi, G.; Vitale, P. Cheap and Environmentally Sustainable Stereoselective Arylketones Reduction by Lactobacillus reuteri Whole Cells. J. Mol. Catal. B: Enzym. 2016, 124, 29–37. DOI: 10.1016/j.molcatb.2015.11.025.
   Google Scholar
• Li, H.; Li, Z.; Ruan, G.; Yu, Y.; Liu, X. Asymmetric Reduction of Acetophenone into R-(+)-1-phenylethanol by Endophytic Fungus Neofusicoccum parvum BYEF07 Isolated from Illicium verum. Biochem. Biophys. Res. Commun. 2016, 473, 874–878. DOI: 10.1016/j.bbrc.2016.03.142.
   PubMed Web of Science ®Google Scholar
• Kumar, S.; Stecher, G.; Li, M.; Knyaz, C.; Tamura, K. MEGA X: Molecular Evolutionary Genetics Analysis across Computing Platforms. Mol. Biol. Evol. 2018, 35, 1547–1549. DOI: 10.1093/molbev/msy096.
   PubMed Web of Science ®Google Scholar
• Çolak, N. S.; Şahin, E.; Dertli, E.; Yilmaz, M. T.; Taylan, O. Response Surface Methodology as Optimization Strategy for Asymmetric Bioreduction of Acetophenone Using Whole Cell of Lactobacillus senmaizukei. Prep. Biochem. Biotechnol. 2019, 49, 884–890. DOI: 10.1080/10826068.2019.1633668.
   PubMed Web of Science ®Google Scholar
• Şahin, E. Candida Zeylanoides as Whole-Cell Biocatalyst to Perform Asymmetric Bioreduction of Benzophenone Derivatives. Synth. Commun. 2020, 50, 612–619. DOI: 10.1080/00397911.2019.1710213.
   Web of Science ®Google Scholar
• Şahin, E. Production of Enantiopure Chiral Aryl Heteroaryl Carbinols using Whole-cell Lactobacillus paracasei Biotransformation: Synthetic Communications. Synth. Commun. 50, 549–557.
   Google Scholar
• Şahin, E. First Green Synthesis of (R)-2-Methyl-1-Phenylpropan-1-Ol Using Whole-Cell Lactobacillus Paracasei BD101 Biotransformation. Biocatal. Biotransform. 2020, 38, 138–143. DOI: 10.1080/10242422.2019.1698554.
   Web of Science ®Google Scholar
• Nakamura, K.; Matsuda, T. Biocatalytic Reduction of Carbonyl Groups. Coc. 2006, 10, 1217–1246. DOI: 10.2174/138527206777698020.
   Google Scholar
• Upadhyaya Joshi, B.; Singh, P.; Saini, H. S. Optimization of Culture Conditions for Enhanced Asymmetric Bioreduction of Acetophenone and Its Derivatives by Growing Cells of Pseudomonas sp. AP1. Biocatal. Agric. Biotechnol. 2014, 3, 142–148. DOI: 10.1016/j.bcab.2014.07.005.
   Google Scholar
• Singh, S.; Jothi, S.; Despande, S.; Lal, S.; Desai, S. Fungus Mediated Stereo-Selective Bioreduction of Keto Intermediates of Pharmaceutically Active Compounds to Their Corresponding Hydroxy Compounds. WO2015071861A2, May 21, 2015.
   Google Scholar