Browse > Article
http://dx.doi.org/10.4014/jmb.1711.11036

Preparation of Interface-Assembled Carbonyl Reductase and Its Application in the Synthesis of S-Licarbazepine in Toluene/Tris-HCl Buffer Biphasic System  

Ou, Zhimin (Pharmaceuticals College, Zhejiang University of Technology)
Xu, Jiahui (Pharmaceuticals College, Zhejiang University of Technology)
Du, Lihua (Pharmaceuticals College, Zhejiang University of Technology)
Tang, Lan (Pharmaceuticals College, Zhejiang University of Technology)
Niu, Yangping (Linan People's Hospital)
Cui, Jian (Linan People's Hospital)
Publication Information
Journal of Microbiology and Biotechnology / v.28, no.4, 2018 , pp. 613-621 More about this Journal
Abstract
In this study, interface-assembled carbonyl reductase (IACR) was prepared and used in the synthesis of S-licarbazepine in a toluene/Tris-HCl biphasic system. The carbonyl reductase (CR) was conjugated with polystyrene to form a surfactant-like structure at the interface of the toluene/Tris-HCl biphasic system. The interface-assembled efficiency of IACR reached 83% when the CR (180 U/mg) and polystyrene concentration were $8{\times}10^2g/ml$ and $3.75{\times}10^3g/ml$, respectively. The conversion reached 95.6% and the enantiometric excess of S-licarbazepine was 98.6% when $3.97{\times}10^6nmol/l$ oxcarbazepine was converted by IACR using 6% ethanol as a co-substrate in toluene/Tris-HCl (12.5:10) at $30^{\circ}C$ and $43{\times}g$ for 6 h. IACR could be reused efficiently five times.
Keywords
Asymmetric reduction; interface-assembled carbonyl reductase; oxcarbazepine; polystyrene; S-licarbazepine;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Ravinder B, Reddy SR, Sridhar M, Mohan MM, Srinivas K, Reddy AP. 2013. An efficient synthesis for eslicarbazepine acetate, oxcarbazepine, and carbazepine. Tetrahedron Lett. 54: 2841-2844.   DOI
2 Desai SJ, Pandya AK, Sawant SP, Mehariya KR. Process for preparation of enantiomers of licarbazepine. WIPO Patent Application WO/2011/117885.
3 Li HY, Li ZY, Ruan GH, Yu YK, Liu XM. 2016. Asymmetric reduction of acetophenone into R-(+)-1-phenylethanol by endophytic fungus Neofusicoccum parvum BYEF07 isolated from Illicium verum. Biochem. Biophs. Res. Commun. 473: 874-878.   DOI
4 Birolli WG, Ferreira IM, Alvarenga N, Santos DA, Matos IL, Comasseto JV, et al. 2015. Biocatalysis and biotransformation in Brazil: an overview. Biotechnol. Adv. 33: 481-510.   DOI
5 Singh M, Singh S, Deshaboina S, Krishnen H, Lloyd R, Holt-Tiffin K, et al. 2012. Asymmetric reduction of a key intermediate of eslicarbazepine acetate using whole cell biotransformation in a biphasic medium. Catal. Sci. Tech. 2: 1602-1605.   DOI
6 Shen L, Cheng KCK, Schroeder MK, Yang P, Marsh ENG, Lahann J, et al. 2016. Immobilization of enzyme on a polymer surface. Surf. Sci. 648: 53-59.   DOI
7 Wang LF, Zhu GY, Wang P, Zhang NB. 2005. Self-assembling of polymer-enzyme conjugates at oil/water interfaces. Biotechnol. Prog. 21: 1321-1328.
8 Fainerman VB, Miller R. 2005. Equilibrium and dynamic characteristics of protein adsorption layers at gas-liquid interfaces: theoretical and experimental data. Colloid J. 67: 393-404.   DOI
9 Zhu GY, Wang P. 2004. Polymer-enzyme conjugates can self-assemble at oil/water interfaces and effect interfacial biotransformations. J. Am. Chem. Soc. 126: 11132-11133.   DOI
10 Barbosa CG, Caseli L, Peres LO. 2016. Conjugated polymers nanostructured as smart interfaces for controlling the catalytic properties of enzymes. J. Colloid Interface Sci. 76: 206-213.
11 Liu H, Zhang J, Luo X, Kong N, Cui L, Liu J. 2013. Preparation of biodegradable and thermoresponsive enzyme-polymer conjugates with controllable bioactivity via RAFT polymerization. Eur. Polym. J. 49: 2949-2960.   DOI
12 Bradford MM. 1976. Rapid and sensitive method for the quantitation of microgram quantities of protein: the principle of protein-dye binding. Anal. Biochem. 72: 248-255.   DOI
13 Choi JM, Han SS, Kim HS. 2015. Industrial applications of enzyme biocatalysis: current status and future aspects. Biotechnol. Adv. 33: 1443-1454.   DOI
14 Rodriguez C, Lavandera I, Gotor V. 2012. Recent advances in cofactor regeneration systems applied to biocatalyzed oxidative processes. Curr. Org. Chem. 16: 2525-2541.   DOI
15 Muthineni N, Arnipally MS, Bojja S, Meshram HM, Adari BR. 2016. A green approach towards the synthesis of chiral alcohols using functionalized alginate immobilized Saccharomyces cerevisiae cells. J. Mol. Catal. B Enzym. 134: 233-237.   DOI
16 Biton V, Rogin JB, Krauss G, Aboukhalil B, Rocha JF, Moreira J, et al. 2017. Adjunctive eslicarbazepine acetate: a pooled analysis of three phase III trials. Epilepsy Behav. 72: 127-134.   DOI
17 Liu ZQ, Dong SC, Yin HH, Xue YP, Tang XL, Zhang XJ, et al. 2017. Enzymatic synthesis of an ezetimibe intermediate using carbonyl reductase coupled with glucose dehydrogenase in an aqueous-organic solvent system. Bioresour. Technol. 229: 26-32.   DOI
18 Philips RS. 1996. Temperature modulation of the stereochemistry of enzymatic catalysis: prospects for exploitation. Trends Biotechnol. 14: 13-16.   DOI
19 Xie Q, Wu JP, Lin L, Xu G, Yang LR. 2009. Purification and characterization of a carbonyl reductase from Candida pseudotropicalis. J. Chem. Eng. Chin. Univ. 23: 92-98.
20 Liu L, Zhang C, Guo WB, Xu L. 2016. Improved synthesis of eslicarbazepine acetate. Chin. J. Med. Chem. 26: 31-36.
21 Servais AC, Janicot B, Takam A, Crommen J, Fillet M. 2016. Liquid chromatography separation of the chiral prodrug eslicarbazepine acetate and its main metabolites in polar organic mode. Application to their analysis after in vitro metabolism. J. Chromatogr. A 1467: 306-311.   DOI
22 Modukuru NK, Sukumaran J, Steven J, Chan AS, Gohel A. 2014. Development of a practical, biocatalytic reduction for the manufacture of S-licarbazepine using an evolved ketoreductase. Org. Process Res. Dev. 18: 810-815.   DOI
23 Ou ZM, Shi HB, Sun XY, Shen WH. 2011. Synthesis of S-licarbazepine by asymmetric reduction of oxcarbazepine with Saccharomyces cerevisiae CGMCC No. 2266. J. Mol. Catal. B Enzyme 72: 294-297.   DOI