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Received December 17, 2020
Accepted February 1, 2021
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Optimum synthesis of esomeprazole catalyzed by Rhodococcus rhodochrous ATCC 4276 through response surface methodology
Yuanyuan Zhang1 2†
Qiuxiang Zhao1 2
Hui Tang1 3
Huiling Li1 3
Depeng Li1 4
Zhiyong Wang1 3
Xin Gao1 4†
Fanye Wang1 3
1State Key Laboratory Base for Eco-Chemical Engineering in College of Chemical Engineering, Qingdao University of Science and Technology, Mail box 70, 53 Zhengzhou Road, Qingdao 266042, China 2William G. Lowrie Department of Chemical and Biomolecular Engineering, The Ohio State University, 151 West Woodruff Avenue, Columbus, Ohio 43210, USA 3Department of Pharmaceutical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Mail Box 70, 53 Zhengzhou Road, Qingdao 266042, China 4Kekulé-Institut für Organis che Chemie und Biochemieder Rheinischen Friedrich-Wilhelms-Universität, BonnGerhard-Domagk-Str.153121 Bonn Germany
Korean Journal of Chemical Engineering, May 2021, 38(5), 989-996(8), 10.1007/s11814-021-0757-9
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Abstract
Enantiopure esomeprazole is an important drug in the treatment of gastric ulcer. The asymmetric sulfoxidation of omeprazole thioether was catalyzed by immobilized cells of a mutant of Rhodococcus rhodocrous ATCC 4276 to synthesize esomeprazole. The bioreaction was carried out in a biphasic system (chloroform-water), at a high substrate concentration (200mM), and optimized using response surface methodology (RSM). The optimal yield of esomeprazole obtained was 94.8% with e.e. (>99%) without the formation of the sulfone form as a byproduct, under the optimal conditions: the concentration of immobilized cells, 283.5 g/L, the incubation temperature, 37.05 °C, and pH of phosphate buffer, 7.35, respectively. A quadratic polynomial model was developed with R2 of 0.9998, which indicates that the model predicts the observed data with very high accuracy. The mutant exhibited a high enantioselective activity and substrate and product tolerance. The small size of immobilized cell beads (0.5-1 mm) creates a large reaction interface. The aerated flask provides enough oxygen for a high concentration of cells. The significant improvement of substrate tolerance may mainly be attributed to employing the chloroform-water biphasic system because organic substrates may be partitioned in the organic phase, eliminating potential damage and inhibition to cells. Based on the above, the asymmetric sulfoxidation catalyzed by immobilized bacterial cells is therefore more promising for efficient synthesis of chiral sulfoxides.
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References
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Ozaki S, Matsui T, Watanabe Y, J. Am. Chem. Soc., 119(28), 6666 (1997)
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Borges KB, de Souza Borges W, Duran-Patron R, Pupo MT, Bonato PS, Collado IG, Tetrahedron: Asymmetry, 20, 385 (2009)
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Yoshida T, Kito M, Tsujii M, Nagasawa T, Biotechnol. Lett., 23(15), 1217 (2001)
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Kuyukina MS, Ivshina IB, Gavrin AY, Podorozhko EA, Philp JC, J. Microbiol. Methods, 65, 596 (2006)
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He JY, Sun ZH, Ruan WQ, Xu Y, Process Biochem., 41(1), 244 (2006)
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Seenivasaperumal M, Federsel HJ, Szab K, Adv. Synth. Catal., 351, 903 (2010)
Holland HL, Rand CG, Viski P, Brown FM, Can. J. Chem., 69, 1989 (1991)
Tarasova EV, Grishko VV, Ivshina IB, Process Biochem., 52, 1 (2016)
Aguirre-Pranzoni C, Bisogno FR, Orden AA, Kurina-Sanz M, J. Mol. Catal. B-Enzym., 114, 19 (2015)
Grishko VV, Tarasova EV, Ivshina IB, Process Biochem., 48(11), 1640 (2013)
De Gonzalo G, Mascotti ML, Orden AA, Bisogno FR, Kurina-Sanz M, J. Mol. Catal. B-Enzym., 82, 32 (2012)
Holland HL, Brown FM, Larsen BG, Zabic M, Tetrahedron: Asymmetry, 6, 1569 (1995)
Bhasarkar JB, Dikshit PK, Moholkar VS, Bioresour. Technol., 187, 369 (2015)
He YC, Ma CL, Yang ZX, Zhou M, Xing Z, Ma JT, Yu HL, Appl. Microbiol. Biotechnol., 97(24), 10329 (2013)
He YC, Zhou Q, Ma CL, Cai ZQ, Wang LQ, Zhao XY, Chen Q, Gao DZ, Zheng M, Wang XD, Sun Q, Bioresour. Technol., 115, 88 (2012)
Li YN, Shi XA, Zong MH, Meng C, Dong YQ, Guo YH, Enzyme Microb. Technol., 40(5), 1305 (2007)
Lou WY, Zong MH, Smith TJ, Green Chem., 8, 147 (2006)
Waghmare GV, Chatterji A, Rathod VK, Appl. Biochem. Biotechnol., 183(3), 792 (2017)
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de Miranda AS, Miranda LSM, de Souza ROMA, Biotechnol. Adv., 33, 372 (2015)
Mathpati AC, Badgujar KC, Bhanage BM, Enzyme Microb. Technol., 84, 1 (2016)
Luo DH, Zong MH, Xu JH, J. Mol. Catal. B-Enzym., 24, 83 (2003)
