Catalytic Function and Application of Cytochrome P450 Enzymes in Biosynthesis and Organic Synthesis
- Corresponding author: Li Shengying, lishengying@qibebt.ac.cn
Citation: Jiang Yuanyuan, Li Shengying. Catalytic Function and Application of Cytochrome P450 Enzymes in Biosynthesis and Organic Synthesis[J]. Chinese Journal of Organic Chemistry, ;2018, 38(9): 2307-2323. doi: 10.6023/cjoc201805055
(a) Urlacher, V. B.; Girhard, M. Trends Biotechnol. 2012, 30, 26.
(b) Keasling, J. D.; Mendoza, A.; Baran, P. S. Nature 2012, 492, 188.
Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611.
Mcintosh, J. A.; Farwell, C. C.; Arnold, F. H. Curr. Opin. Chem. Biol. 2014, 19, 126.
doi: 10.1016/j.cbpa.2014.02.001
Arnold, F. H. Angew. Chem., Int. Ed. 2017. 56, 4143.
Denisov, I. G.; Maris, T. M.; Sligar, S. G.; Schlichting, I. Chem. Rev. 2005, 105, 2253.
doi: 10.1021/cr0307143
(a) Lu, A. Y.; Coon, M. J. J. Biol. Chem. 1968, 243, 1331.
(b) Hildebrandt, A.; Remmer, H.; Estabrook, R. W. Biochem. Biophys. Res. Commun. 1968, 30, 607.
Li, Z.; Zhang, W.; Li, S. Y. Acta Microbiol. Sin. 2016, 56, 496(in Chinese).
Nebert, D. W.; Adesnik, M.; Coon, M. J.; Estabrook, R. W.; Gonzalez, F. J.; Guengerich, F. P.; Gunsalus, I. C.; Johnson, E. F.; Kemper, B.; Levin, W. DNA 1987, 6, 1.
Ruettinger, R. T.; Fulco, A. J. J. Biol. Chem. 1981, 256, 5728.
Daiber, A.; Shoun, H.; Ullrich, V. J. Inorg. Biochem. 2005, 99, 185.
Hasemann, C. A.; Kurumbail, R. G.; Boddupalli, S. S.; Peterson, J. A.; Deisenhofer, J. Structure 1995, 3, 41.
doi: 10.1016/S0969-2126(01)00134-4
Presnell, S. R.; Cohen, F. E. Proc. Natl. Acad. Sci. U. S. A. 1989, 86, 6592.
Gotoh, O. J. Biol. Chem. 1992, 267, 83.
Pylypenko, O.; Schlichting, I. Annu. Rev. Biochem. 2004, 73, 991.
doi: 10.1146/annurev.biochem.73.011303.073711
(a) Conrad, H. E.; Lieb, K.; Gunsalus, I. C. J. Biol. Chem. 1965, 240, 4029.
(b) Katagiri, M.; Ganguli, B. N.; Gunsalus, I. C. J. Biol. Chem. 1968, 243, 3543.
(a) Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A. M.; Maves, S. A.; Benson, D. E.; Sweet, R. M.; Ringe, D.; Petsko, G. A.; Sligar, S. G. Science 2000, 287, 1615.
(b) Groves, J. T. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 3569.
(c) Shaik, S.; Cohen, S.; Wang, Y.; Chen, H.; Kumar, D.; Thiel, W. Chem. Rev. 2010, 110, 949.
(d) Guengerich, F. P. J. Biochem. Mol. Toxicol. 2007, 21, 163.
Montellano, P. O. D. Cytochrome P450:Structure, Mechanism, and Biochemistry, 4th ed., Springer International Publishing, Switzerland, 2015, p. 1.
Rude, M. A.; Baron, T. S.; Brubaker, S.; Alibhai, M.; Cardayre, S. B. D.; Schirmer, A. Appl. Environ. Microbiol. 2011, 77, 1718.
(a) Cryle, M. J.; De Voss, J. J. Angew. Chem., Int. Ed. 2006, 45, 8221.
(b) Jin, S.; Makris, T. M.; Bryson, T. A.; Sligar, S. G.; Dawson, J. H. J. Am. Chem. Soc. 2003, 125, 3406.
Barry, S. M.; Kers, J. A.; Johnson, E. G.; Song, L.; Aston, P. R.; Bhumit, P.; Krasnoff, S. B.; Crane, B. R.; Gibson, D. M.; Rosemary, L. Nat. Chem. Biol. 2012, 8, 814.
Zhang, X.; Li, S. Nat. Prod. Rep. 2017, 34, 1061.
doi: 10.1039/C7NP00028F
Zhu, G. D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877.
doi: 10.1021/cr00038a007
Kawauchi, H.; Sasaki, J.; Adachi, T.; Hanada, K.; Beppu, T.; Horinouchi, S. Biochim. Biophys. Acta 1994, 1219, 179.
doi: 10.1016/0167-4781(94)90266-6
Yasutake, Y.; Fujii, Y.; Cheon, W. K.; Arisawa, A.; Tamura, T. Acta Crystallogr. 2009, 65, 372.
Peters, M. W.; Meinhold, P.; Glieder, A.; Arnold, F. H. J. Am. Chem. Soc. 2003, 125, 13442.
doi: 10.1021/ja0303790
Xu, F.; Bell, S. G.; Lednik, J.; Insley, A.; Rao, Z.; Wong, L. L. Angew. Chem., Int. Ed. 2005, 117, 4097.
Du, L.; Dong, S.; Zhang, X.; Jiang, C.; Chen, J.; Yao, L.; Wang, X.; Wan, X.; Liu, X.; Wang, X.; Huang, S.; Cui, Q.; Feng, Y.; Liu, S.; Li, S. Proc. Natl. Acad. Sci. U. S. A. 2017, 114, E5129.
Woodley, J. M. Trends Biotechnol. 2008, 26, 321.
doi: 10.1016/j.tibtech.2008.03.004
Ogura, H.; Nishida, C. R.; Hoch, U. R.; Perera, R.; Dawson, J. H.; Pr, O. D. M. Biochemistry 2004, 43, 14712.
(a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
(b) Islam, S. M.; Roy, A. S.; Mondal, P.; Mobarok, M.; Roy, B.; Salam, N.; Paul, S.; Mondal, S. Monatsh. Chem. 2012, 143, 815.
Kubo, T.; Peters, M. W.; Meinhold, P.; Arnold, F. H. Chemistry 2006, 12, 1216.
(a) Podust, L. M.; Sherman, D. H. Nat. Prod. Rep. 2012, 29, 1251.
(b) Li, S.; Tietz, D. R.; Rutaganira, F. U.; Kells, P. M.; Anzai, Y.; Kato, F.; Pochapsky, T. C.; Sherman, D. H.; Podust, L. M. J. Biol. Chem. 2012, 287, 37880.
Anzai, Y.; Li, S.; Chaulagain, M. R.; Kinoshita, K.; Kato, F.; Montgomery, J.; Sherman, D. H. Chem. Biol. 2008, 15, 950.
doi: 10.1016/j.chembiol.2008.07.014
Chooi, Y. H.; Hong, Y. J.; Cacho, R. A.; Tantillo, D. J.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 16805.
doi: 10.1021/ja408966t
Coelho, P. S.; Brustad, E. M.; Kannan, A.; Arnold, F. H. Science 2013, 339, 307.
Halo, L. M.; Heneghan, M. N.; Yakasai, A. A.; Song, Z.; Williams, K.; Bailey, A. M.; Cox, R. J.; Lazarus, C. M.; Simpson, T. J. J. Am. Chem. Soc. 2008, 130, 17988.
doi: 10.1021/ja807052c
Tsunematsu, Y.; Ishikawa, N.; Wakana, D.; Goda, Y.; Noguchi, H.; Moriya, H.; Hotta, K.; Watanabe, K. Nat. Chem. Biol. 2013, 9, 818.
Guengerich, F. P.; Munro, A. W. J. Biol. Chem. 2013, 288, 17065.
Mizutani, M.; Sato, F. Arch. Biochem. Biophys. 2011, 507, 194.
Gesell, A.; Rolf, M.; Ziegler, J.; Díaz Chávez, M. L.; Huang, F. C.; Kutchan, T. M. J. Biol. Chem. 2009, 284, 24432.
Ikezawa, N.; Iwasa, K.; Sato, F. J. Biol. Chem. 2008, 283, 8810.
Mazzaferro, L. S.; Hüttel, W.; Fries, A.; Müller, M. J. Am. Chem. Soc. 2015, 137, 12289.
doi: 10.1021/jacs.5b06776
Kraus, P. F.; Kutchan, T. M. Proc. Natl. Acad. Sci. U. S. A. 1995, 92, 2071.
Irmler, S.; Schroder, G.-P. B.; Crouch, N. P.; Hotze, M.; Schmidt, J. Plant J. 2000, 24, 797.
Lin, H. C.; Chooi, Y. H.; Dhingra, S.; Xu, W.; Calvo, A. M.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 4616.
Akashi, T.; Aoki, T.; Ayabe, S. FEBS Lett. 1998, 431, 287.
Li, R.; Reed, D. W.; Liu, E.; Nowak, J.; Pelcher, L. E.; Page, J. E.; Covello, P. S. Chem. Biol. 2006, 13, 513.
(a) Brosen, K. Drug Metabol. Pers. Ther. 2015, 30, 147.
(b) Morinobu, S.; Tanaka, T.; Kawakatsu, S.; Totsuka, S.; Koyama, E.; Chiba, K.; Ishizaki, T.; Kubota, T. Psychiatry Clin. Neurosci. 1997, 51, 253.
Yu, F.; Li, M.; Xu, C.; Wang, Z.; Zhou, H.; Yang, M.; Chen, Y.; Tang, L.; He, J. PloS One 2013, 8, e81526.
Prier, C. K.; Zhang, R. K.; Buller, A. R.; Brinkmannchen, S.; Arnold, F. H. Nat. Chem. 2017, 9, 629.
Mcintosh, J. A.; Coelho, P. S.; Farwell, C. C.; Wang, Z. J.; Lewis, J. C.; Brown, T. R.; Arnold, F. H. Angew. Chem., Int. Ed. 2013, 52, 9309.
Hammer, S. C.; Kubik, G.; Watkins, E.; Huang, S.; Minges, H.; Arnold, F. H. Science 2017, 358, 215.
doi: 10.1126/science.aao1482
Li, A.; Wang, B.; Ilie, A.; Dubey, K. D.; Bange, G.; Korendovych, I. V.; Shaik, S.; Reetz, M. T. Nat. Commun. 2017, 8, 14876.
doi: 10.1038/ncomms14876
Kan, S. B.; Lewis, R. D.; Chen, K.; Arnold, F. H. Science 2016, 354, 1048.
doi: 10.1126/science.aah6219
(a) Mcreynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 35, 2239.
(b) Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.
Ma, N.; Chen, Z.; Chen, J.; Chen, J.; Wang, C.; Zhou, H.; Yao, L.; Shoji, O.; Watanabe, Y.; Cong, Z. Angew. Chem., Int. Ed. 2018, 57, 7628.
Bornscheuer, U. T. Angew. Chem., Int. Ed. 1998, 37, 65.
Yang, J.; Ruff, A. J.; Arlt, M.; Schwaneberg, U. Biotechnol. Bioeng. 2017, 114, 1921.
Georgescu, R.; Bandara, G.; Sun, L. Methods Mol. Biol. 2003, 231, 75.
Crameri, A.; Raillard, S. A.; Bermudez, E.; Stemmer, W. P. Nature 1998, 391, 288.
doi: 10.1038/34663
Reetz, M. T.; Carballeira, J. D. Nat. Protoc. 2007, 2, 891.
doi: 10.1038/nprot.2007.72
Reetz, M. T.; Bocola, M.; Carballeira, J. D.; Zha, D.; Vogel, A. Angew. Chem., Int. Ed. 2010, 117, 4264.
Roiban, G. D.; Reetz, M. T. Chem. Commun. 2015, 51, 2208.
Warman, A. J.; Roitel, O.; Neeli, R.; Girvan, H. M.; Seward, H. E.; Murray, S. A.; Mclean, K. J.; Joyce, M. G.; Toogood, H.; Holt, R. A. Biochem. Soc. Trans. 2005, 33, 747.
Kille, S.; Zilly, F. E.; Acevedo, J. P.; Reetz, M. T. Nat. Chem. 2011, 3, 738.
Chen, K.; Huang, X.; Kan, S.; Zhang, R. K.; Arnold, F. H. Science 2018, 360, 71.
Wong, L. L.; Whitehouse, C. J. C.; Yang, W.; Yorke, J. A.; Blanford, C. F.; Bell, S. G.; Bartlam, M.; Rao, Z. Drug Metab. Rev. 2010, 11, 2549.
Seifert, A.; Vomund, S.; Grohmann, K.; Kriening, S.; Urlacher, V. B.; Laschat, S.; Pleiss, J. ChemBioChem 2009, 10, 1426.
Sherman, D. H.; Li, S.; Yermalitskaya, L. V.; Kim, Y.; Smith, J. A.; Waterman, M. R.; Podust, L. M. J. Biol. Chem. 2006, 281, 26289.
Vermeulen, N. P. E.; Graaf, C. D.; Stjernschantz, E.; Feenstra, A.; Oostenbrink, B. C. International Society for the Study of Xenobiotics Meeting, Sendai, Japan, 2007, pp. 223~232.
Morigasaki, S.; Takata, K.; Sanada, Y.; Wada, K.; Yee, B. C.; Shin, S.; Buchanan, B. B. Arch. Biochem. Biophys. 1990, 283, 75.
Sibbesen, O.; De Voss, J. J.; Montellano, P. R. J. Biol. Chem. 1996, 271, 22462.
Lambeth, J. D.; Seybert, D. W.; Kamin, H. J. Biol. Chem. 1980, 255, 4667.
Neunzig, I.; Widjaja, M.; Peters, F. T.; Maurer, H. H.; Hehn, A.; Bourgaud, F.; Bureik, M. Appl. Biochem. Biotechnol. 2013, 170, 1751.
doi: 10.1007/s12010-013-0303-2
Ma, L.; Du, L.; Chen, H.; Sun, Y.; Huang, S.; Zheng, X.; Kim, E. S.; Li, S. Appl. Environ. Microbiol. 2015, 81, 6268.
Zhang, W.; Liu, Y.; Yan, J.; Cao, S.; Bai, F.; Yang, Y.; Huang, S.; Yao, L.; Anzai, Y.; Kato, F.; Podust, L. M.; Sherman, D. H.; Li, S. J. Am. Chem. Soc. 2014, 136, 3640.
Liu, Y.; Wang, C.; Yan, J.; Zhang, W.; Guan, W.; Lu, X.; Li, S. Biotechnol. Biofuels 2014, 256, 130.
Ro, D. K.; Paradise, E. M.; Ouellet, M.; Fisher, K. J.; Newman, K. L.; Ndungu, J. M.; Ho, K. A.; Eachus, R. A.; Ham, T. S.; Kirby, J. Nature 2006, 440, 940.
(a) Chefson, A.; Auclair, K. Mol. BioSyst. 2006, 2, 462.
(b) Schewe, H.; Holtmann, D.; Schrader, J. Appl. Microbiol. Biotechnol. 2009, 83, 849.
Shrestha, P.; Oh, T. J.; Sohng, J. K. Biotechnol. Lett. 2008, 30, 1101.
Li, S.; Chaulagain, M. R.; Knauff, A. R.; Podust, L. M.; Montgomery, J.; Sherman, D. H. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 18463.
Narayan, A. R.; Jiménez-Osés, G.; Liu, P; Negretti, S.; Zhao, W; Gilbert, M. M.; Ramabhadran, R. O.; Yang, Y. F.; Furan, L. R.; Li, Z.; Podust, L. M.; Montgomery, J.; Houk, K. N.; Sherman, D. H. Nat. Chem. 2015, 7, 653.
Key, H. M.; Dydio, P.; Clark, D. S.; Hartwig, J. F. Nature 2016, 534, 534.
Hansen, D. A.; Rath, C. M.; Eisman, E. B.; Narayan, A. R.; Kittendorf, J. D.; Mortison, J. D.; Yoon, Y. J.; Sherman, D. H. J. Am. Chem. Soc. 2013, 135, 11232.
(a) Perez, D. I.; Grau, M. M.; Arends, I. W. C. E.; Hollmann, F. Chem. Commun. 2010, 41, 6848.
(b) Girhard, M.; Kunigk, E.; Tihovsky, S.; Shumyantseva, V. V.; Urlacher, V. B. Biotechnol. Appl. Biochem. 2013, 60, 111.
(c) Paul, C. E.; Churakova, E.; Maurits, E.; Girhard, M.; Urlacher, V. B.; Hollmann, F. Biorg. Med. Chem. 2014, 22, 5692.
Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010
Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
Yuan Zheng , Quan Lan , Zhenggen Zha , Lingling Li , Jun Jiang , Pingping Zhu . Teaching Reform of Organic Synthesis Experiments by Introducing Reverse Thinking and Design Concepts: Taking the Synthesis of Cinnamic Acid Based on Retrosynthetic Analysis as an Example. University Chemistry, 2024, 39(6): 207-213. doi: 10.3866/PKU.DXHX202310065
Yang Liu , Peng Chen , Lei Liu . Chemistry “101 Plan”: Design and Construction of Chemical Biology Textbook. University Chemistry, 2024, 39(10): 45-51. doi: 10.12461/PKU.DXHX202407085
Tianyu Feng , Guifang Jia , Peng Zou , Jun Huang , Zhanxia Lü , Zhen Gao , Chu Wang . Construction of the Chemistry Biology Experiment Course in the Chemistry “101 Program”. University Chemistry, 2024, 39(10): 69-77. doi: 10.12461/PKU.DXHX202409002
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
Jiarui Wu , Gengxin Wu , Yan Wang , Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014
Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Weihua Jiang , Yongsheng Zhou , Qiaoqiao Teng . Progressive Teaching Model in the Practice and Exploration of Ideological and Political Education in Laboratory Courses: Taking the Organic Chemistry Experiment “Synthesis of Aspirin” as an Example. University Chemistry, 2024, 39(2): 99-104. doi: 10.3866/PKU.DXHX202306028
(a) The crystal structure with secondary structures; (b) the substrate recognition sites, SRS1, SRS2, SRS3, SRS4, SRS5, and SRS6