Heterologous expression and characterization of plant Taxadiene-5α-Hydroxylase (CYP725A4) in Escherichia coli

Protein Expression and Purification - Tập 132 - Trang 60-67 - 2017
John Edward Rouck1, Bradley Walters Biggs2,3, Amogh Kambalyal1, William R. Arnold1, Marjan De Mey4, Parayil Kumaran Ajikumar2, Aditi Das1
1Department of Comparative Biosciences, Department of Biochemistry, Department of Bioengineering, Division of Nutritional Science, Center for Biophysics and Quantitative Biology, Beckman Institute for Advanced Science and Technology, University of Illinois Urbana-Champaign, Urbana, IL 61801, USA
2Manus Biosynthesis, 1030 Massachusetts Avenue, Suite 300, Cambridge, MA 02138, USA
3Department of Chemical and Biological Engineering, Northwestern University, Evanston, IL 60208, USA
4Centre for Industrial Biotechnology and Biocatalysis, Ghent University, Coupure Links 653, B-9000, Belgium

Tài liệu tham khảo

Hefner, 1996, Cytochrome P450-catalyzed hydroxylation of taxa-4(5),11(12)-diene to taxa-4(20),11(12)-dien-5alpha-ol: the first oxygenation step in taxol biosynthesis, Chem. Biol., 3, 479, 10.1016/S1074-5521(96)90096-4 Li, 2008, Studies on taxol biosynthesis: preparation of taxadiene-diol- and triol-derivatives by deoxygenation of taxusin, Tetrahedron, 64, 6561, 10.1016/j.tet.2008.04.008 Lokeshwar, 1995, Enhancement of radiation response of prostatic carcinoma by taxol: therapeutic potential for late-stage malignancy, Anticancer Res., 15, 93 Xu, 2013, Engineering plant metabolism into microbes: from systems biology to synthetic biology, Curr. Opin. Biotechnol., 24, 291, 10.1016/j.copbio.2012.08.010 Marienhagen, 2013, Metabolic engineering of microorganisms for the synthesis of plant natural products, J. Biotechnol., 163, 166, 10.1016/j.jbiotec.2012.06.001 Keasling, 2012, Synthesis: a constructive debate, Nature, 492, 188, 10.1038/492188a Keasling, 2010, Manufacturing molecules through metabolic engineering, Science, 330, 1355, 10.1126/science.1193990 Pickens, 2011, Metabolic engineering for the production of natural products, Annu. Rev. Chem. Biomol. Eng., 2, 211, 10.1146/annurev-chembioeng-061010-114209 Ajikumar, 2010, Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli, Science, 330, 70, 10.1126/science.1191652 Biggs, 2016, Overcoming heterologous protein interdependency to optimize P450-mediated Taxol precursor synthesis in Escherichia coli, Proc. Natl. Acad. Sci., 113, 3209, 10.1073/pnas.1515826113 Jennewein, 2004, Cytochrome p450 taxadiene 5alpha-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis, Chem. Biol., 11, 379, 10.1016/j.chembiol.2004.02.022 Rontein, 2008, CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5),11(12)-diene into the cyclic ether 5(12)-oxa-3(11)-cyclotaxane, J. Biol. Chem., 283, 6067, 10.1074/jbc.M708950200 Yadav, 2014, Unraveling the multispecificity and catalytic promiscuity of taxadiene monooxygenase, J. Mol. Catal. B Enzym., 110, 154, 10.1016/j.molcatb.2014.10.004 Edgar, 2015, Mechanistic insights into taxadiene epoxidation by taxadiene-5α-hydroxylase, ACS Chem. Biol., 11, 460, 10.1021/acschembio.5b00767 Barton, 2016, Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?, Chem. Sci., 7, 3102, 10.1039/C5SC03463A Biggs, 2016, Orthogonal assays clarify the oxidative biochemistry of Taxol P450 CYP725A4, ACS Chem. Biol., 11, 1445, 10.1021/acschembio.5b00968 Zelasko, 2013, Optimizations to achieve high-level expression of cytochrome P450 proteins using Escherichia coli expression systems, Protein Expr. Purif., 92, 77, 10.1016/j.pep.2013.07.017 McDougle, 2015, Incorporation of charged residues in the CYP2J2 F-G loop disrupts CYP2J2-lipid bilayer interactions, Biochim. Biophys. Acta, 1848, 2460, 10.1016/j.bbamem.2015.07.015 McDougle, 2013, Functional studies of N-terminally modified CYP2J2 epoxygenase in model lipid bilayers, Protein Sci., 22, 964, 10.1002/pro.2280 Hammarström, 2006, Effect of N-terminal solubility enhancing fusion proteins on yield of purified target protein, J. Struct. Funct. Genomics, 7, 1, 10.1007/s10969-005-9003-7 Wang, 1997, Three-dimensional structure of NADPH-cytochrome P450 reductase: prototype for FMN- and FAD-containing enzymes, Proc. Natl. Acad. Sci. U. S. A., 94, 8411, 10.1073/pnas.94.16.8411 Denisov, 2011, Cytochromes P450 in nanodiscs, Biochim. Biophys. Acta, 1814, 223, 10.1016/j.bbapap.2010.05.017 Bayburt, 2010, Membrane protein assembly into Nanodiscs, FEBS Lett., 584, 1721, 10.1016/j.febslet.2009.10.024 Leitz, 2006, Functional reconstitution of Beta2-adrenergic receptors utilizing self-assembling Nanodisc technology, Biotechniques, 40, 601, 10.2144/000112169 Boldog, 2006, Nanodiscs separate chemoreceptor oligomeric states and reveal their signaling properties, Proc. Natl. Acad. Sci., 103, 11509, 10.1073/pnas.0604988103 Nath, 2007, Applications of phospholipid bilayer nanodiscs in the study of membranes and membrane proteins, Biochemistry, 46, 2059, 10.1021/bi602371n Das, 2007, Redox potential control by drug binding to cytochrome P450 3A4, J. Am. Chem. Soc., 129, 13778, 10.1021/ja074864x Duan, 2006, Heterologous expression and strategies for encapsulation of membrane-localized plant P450s, Phytochem. Rev., 5, 507, 10.1007/s11101-006-9009-1 Das, 2009, Modulation of the cytochrome P450 reductase redox potential by the phospholipid bilayer, Biochemistry, 48, 12104, 10.1021/bi9011435 Bayburt, 2003, Self-assembly of single integral membrane proteins into soluble nanoscale phospholipid bilayers. Protein Science, A Publ. Protein Soc., 12, 2476, 10.1110/ps.03267503 Bayburt, 2002, Single-molecule height measurements on microsomal cytochrome P450 in nanometer-scale phospholipid bilayer disks, Proc. Natl. Acad. Sci. U. S. A., 99, 6725, 10.1073/pnas.062565599 Civjan, 2003, Direct solubilization of heterologously expressed membrane proteins by incorporation into nanoscale lipid bilayers, BioTechniques, 35, 556, 10.2144/03353rr02 Duan, 2004, Co-incorporation of heterologously expressed Arabidopsis cytochrome P450 and P450 reductase into soluble nanoscale lipid bilayers, Archives Biochem. Biophysics, 424, 141, 10.1016/j.abb.2004.02.010 McDougle, 2013, Functional studies of N-terminally modified CYP2J2 epoxygenase in model lipid bilayers, Protein Sci., 22, 964, 10.1002/pro.2280 Kelley, 2015, The Phyre2 web portal for protein modeling, prediction and analysis, Nat. Protoc., 10, 845, 10.1038/nprot.2015.053 Humphrey, 1996, VMD: visual molecular dynamics, J. Mol. Graph., 14, 33, 10.1016/0263-7855(96)00018-5 Gonzalez, 1995, Cytochromes P450 expression systems, Annu. Rev. Pharmacol. Toxicol., 35, 369, 10.1146/annurev.pa.35.040195.002101 Larson, 1991, Purification and properties of a shortened form of cytochrome P-450 2E1: deletion of the NH2-terminal membrane-insertion signal peptide does not alter the catalytic activities, Proc. Natl. Acad. Sci. U. S. A., 88, 9141, 10.1073/pnas.88.20.9141 von Wachenfeldt, 1997, Microsomal P450 2C3 is expressed as a soluble dimer inEscherichia coliFollowing modifications of its N-terminus, Archives Biochem. Biophysics, 339, 107, 10.1006/abbi.1996.9859 Richardson, 1995, A universal approach to the expression of human and rabbit cytochrome P450s of the 2C subfamily inEscherichia coli, Archives Biochem. Biophysics, 323, 87, 10.1006/abbi.1995.0013 Barnes, 1991, Expression and enzymatic activity of recombinant cytochrome P450 17 alpha-hydroxylase in Escherichia coli, Proc. Natl. Acad. Sci. U. S. A., 88, 5597, 10.1073/pnas.88.13.5597 Miki, 2014, Biosynthetic pathway for the cyanide-free production of phenylacetonitrile in Escherichia coli by utilizing plant cytochrome P450 79A2 and bacterial aldoxime dehydratase, Appl. Environ. Microbiol., 80, 6828, 10.1128/AEM.01623-14 Guo, 1994, Expression of modified human cytochrome P450 1A1 in Escherichia coli: effects of 5′ substitution, stabilization, purification, spectral characterization, and catalytic properties, Archives Biochem. Biophysics, 312, 436, 10.1006/abbi.1994.1330 Budriang, 2011, An expression of an insect membrane-bound cytochrome P450 CYP6AA3 in the Escherichia coli in relation to insecticide resistance in a malarial vector, Pak. J. Biol. Sci., 14, 466, 10.3923/pjbs.2011.466.475 Müller, 2008, Field-caught permethrin-resistant Anopheles gambiae overexpress CYP6P3, a P450 that metabolises pyrethroids, PLoS Genet., 4, e1000286, 10.1371/journal.pgen.1000286 Larkin, 2007, Clustal W and clustal X version 2.0, Bioinformatics, 23, 2947, 10.1093/bioinformatics/btm404 Al-Gailany, 1978, The role of substrate lipophilicity in determining type 1 microsomal P450 binding characteristics, Biochem. Pharmacol., 27, 783, 10.1016/0006-2952(78)90521-X Baudry, 2003, Molecular docking of substrates and inhibitors in the catalytic site of CYP6B1, an insect cytochrome P450 monooxygenase, Protein Eng., 16, 577, 10.1093/protein/gzg075