Reduction of m-chlorophenacyl chloride coupled with regeneration of NADPH by recombinant Escherichia coli cells co-expressing both carbonyl reductase and glucose 1-dehydrogenase

详细信息    查看全文

• 作者：Tao Yu ; Jian-Fang Li ; Li-Juan Zhu ; Die Hu ; Chao Deng ; Yu-Ting Cai…
• 关键词：m ; Chlorophenacyl chloride ; (R) ; 2 ; Chloro ; 1 ; (3 ; chlorophenyl)ethanol ; Carbonyl reductase ; Glucose 1 ; dehydrogenase ; Co ; expression ; Escherichia coli
• 刊名：Annals of Microbiology
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：66
• 期：1
• 页码：343-350
• 全文大小：738 KB
• 参考文献：Berenguer-Murcia A, Fernandez-Lafuente R (2010) New trends in the recycling of NAD(P)H for the design of sustainable asymmetric reductions catalyzed by dehydrogenases. Curr Org Chem 14:1000–1021CrossRef
  Bloom JD, Dutia MD, Johnson BD, Wissner A, Burns MG, Largis EE, Dolan JA, Claus TH (1992) Disodium (R, R)-5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]-amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate (CL 316,243). A potent β-adrenergic agonist virtually specific for β3 receptors. A promising antidiabetic and antiobesity agent. J Med Chem 35:3081–3084CrossRef PubMed
  Hamada H, Miura T, Kumobayashi H, Matsuda T, Harada T, Nakamura K (2001) Asymmetric synthesis of (R)-2-chloro-1-(m-chlorophenyl)ethanol using acetone powder of Geotrichum candidum. Biotechnol Lett 23:1603–1606CrossRef
  Huisman GW, Collier SJ (2013) On the development of new biocatalytic processes for practical pharmaceutical synthesis. Curr Opin Chem Biol 17:284–292CrossRef PubMed
  Itoh N, Matsuda M, Mabuchi M, Dairi T, Wang JC (2002) Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH. Eur J Biochem 269:2394–2402CrossRef PubMed
  Kizaki N, Yasohara Y, Hasegawa J, Wada M, Kataoka M, Shimizu S (2001) Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes. Appl Microbiol Biotechnol 55:590–595CrossRef PubMed
  Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680–685CrossRef PubMed
  Liang J, Lalonde J, Borup B, Mitchell V, Mundorff E, Trinh N, Kochrekar DA, Cherat RN, Pai GG (2010) Development of a biocatalytic process as an alternative to the (−)-DIP-Cl-mediated asymmetric reduction of a key intermediate of montelukast. Org Process Res Dev 14:193–198CrossRef
  Lin H, Chen YZ, Xu XY, Xia SW, Wang LX (2009) Preparation of key intermediates of adrenergic receptor agonists: Highly enantioselective production of (R)-α-halohydrins with Saccharomyces cerevisiae CGMCC 2.396. J Mol Catal B Enzym 57:1–5CrossRef
  Ni Y, Xu JH (2012) Biocatalytic ketone reduction: a green and efficient access to enantiopure alcohols. Biotechnol Adv 30:1279–1288CrossRef PubMed
  Ni Y, Zhang BH, Sun ZH (2012) Efficient synthesis of (R)-2-chloro-1-(3-chlorophenyl)ethanol by permeabilized whole-cells of Candida ontarioensis. Chin J Catal 33:681–687CrossRef
  Ohkuma T, Tsutsumi K, Utsumi N, Arai N, Noyori R, Murata K (2007) Asymmetric hydrogenation of α-chloro aromatic ketones catalyzed by η 6-arene/TsDPEN–Ruthenium(II) complexes. Org Lett 9:255–257CrossRef PubMed
  Ren J, Dong WY, Yu BQ, Wu QQ, Zhu DM (2012) Synthesis of optically active α
  omohydrins via reduction of α
  omoacetophenone analogues catalyzed by an isolated carbonyl reductase. Tetrahedron Asymmetry 23:497–500CrossRef
  Smith LD, Budgen N, Bungard SJ, Danson MJ, Hough DW (1989) Purification and characterization of glucose dehydrogenase from the thermoacidophilic archaebacterium Thermoplasma acidophilum. Biochem J 261:973–977PubMedCentral CrossRef PubMed
  Solano DM, Hoyos P, Hernáiz MJ, Alcántara AR, Sánchez-Montero JM (2012) Industrial biotransformations in the synthesis of building blocks leading to enantiopure drugs. Bioresour Technol 115:196–207CrossRef
  Su YN, Ni Y, Wang JC, Xu ZH, Sun ZH (2012) Two-enzyme coexpressed recombinant strain for asymmetric synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate. Chin J Catal 33:1650–1660CrossRef
  Wu XR, Jiang JP, Chen YJ (2011) Correlation between intracellular cofactor concentrations and biocatalytic efficiency: coexpression of diketoreductase and glucose dehydrogenase for the preparation of chiral diol for statin drugs. ACS Catal 1:1661–1664CrossRef
  Xia SW, Lin H, Chen YZ (2012) Preparation of (R)-2-chloro-1-(m-chlorophenyl)ethanol by Lipozyme TL IM-catalyzed second resolution. Chin Chem Lett 23:289–292CrossRef
  Yasohara Y, Kizaki N, Hasegawa J, Wada M, Kataoka M, Shimizu S (2000) Molecular cloning and overexpression of the gene encoding an NADPH-dependent carbonyl reductase gene from Candida magnoliae, invoved in stereoselective reduction of ethyl 4-chloro-3-oxobutanoate. Biosci Biotechnol Biochem 64:1430–1436CrossRef PubMed
  Zhang JD, Li AT, Yu HL, Imanaka T, Xu JH (2011) Synthesis of optically pure S-sulfoxide by Escherichia coli transformant cells coexpressing the P450 monooxygenase and glucose dehydrogenase genes. J Ind Microbiol Biotechnol 38:633–641CrossRef PubMed
  Zhang HM, Wang JQ, Wu MC, Gao SJ, Li JF, Yang YJ (2014) Optimized expression, purification and characterization of a family 11 xylanase (AuXyn11A) from Aspergillus usamii E001 in Pichia pastoris. J Sci Food Agric 94:699–706CrossRef PubMed
  Zhou CY, Bai JY, Deng SS, Wang J, Zhu J, Wu MC, Wang W (2008) Cloning of a xylanase gene from Aspergillus usamii and its expression in Escherichia coli. Bioresour Technol 99:831–838CrossRef PubMed
  Zhu DM, Yang Y, Hua L (2006) Stereoselective enzymatic synthesis of chiral alcohols with the use of a carbonyl reductase from Candida magnoliae with anti-Prelog enantioselectivity. J Org Chem 71:4202–4205CrossRef PubMed
  
• 作者单位：Tao Yu (1)
  Jian-Fang Li (2)
  Li-Juan Zhu (1)
  Die Hu (1)
  Chao Deng (3)
  Yu-Ting Cai (3)
  Min-Chen Wu (3)
  
  1. School of Pharmaceutical Science, Jiangnan University, 1800 Lihu Road, Wuxi, 214122, Jiangsu, People’s Republic of China
  2. State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, 214122, Jiangsu, People’s Republic of China
  3. Wuxi Medical School, Jiangnan University, 1800 Lihu Road, Wuxi, 214122, Jiangsu, People’s Republic of China
  
• 刊物主题：Microbiology; Microbial Genetics and Genomics; Microbial Ecology; Fungus Genetics; Medical Microbiology; Applied Microbiology;
• 出版者：Springer Berlin Heidelberg
• ISSN：1869-2044

文摘

Both Sys1 and Sygdh, two codon-optimized genes encoding SyS1 and SyGDH, were synthesized based on the carbonyl reductase (S1) and glucose 1-dehydrogenase (GDH) gene sequences, respectively, from Candida magnoliae and Thermoplasma acidophilum, and co-expressed in Escherichia coli BL21(DE3) using two strategies. One strategy involved a recombinant E. coli strain (E. coli/Sygdh-Sys1) constructed by transforming a recombinant plasmid, pETDuet-Sygdh-Sys1, into E. coli BL21. The other strategy involved another recombinant E. coli strain (E. coli/Sys1/Sygdh) obtained by co-transforming the recombinant plasmids pET-22b-Sys1 and pET-28a-Sygdh into E. coli BL21. The enzyme activity assays indicated that the activities of recombinant SyS1 and SyGDH (3.7 and 56.3 U/g wet cells) expressed in E. coli/Sygdh-Sys1 were higher than those (2.8 and 44.1 U/g wet cells) in E. coli/Sys1/Sygdh. Accordingly, E. coli/Sygdh-Sys1 was chosen, and its whole cells were used as catalysts for the asymmetric reduction of m-chlorophenacyl chloride (m-CPC) to the corresponding (R)-2-chloro-1-(3-chlorophenyl)ethanol [(R)-CCE] coupled with the regeneration of NADPH in situ. Under the optimized reaction conditions of 30 mM m-CPC, 50 mg/ml wet cells, 40 mM glucose and 0.2 mM NADP+ at pH 7.0 and 35 °C for 3 h, (R)-CCE was obtained with a molar yield of 99.2 % and an enantiomeric excess (e.e.) value of more than 99 %. Keywords m-Chlorophenacyl chloride (R)-2-Chloro-1-(3-chlorophenyl)ethanol Carbonyl reductase Glucose 1-dehydrogenase Co-expression Escherichia coli