Selective Hydroxylation of Alkanes Catalyzed by Cytochrome P450 Enzymes

doi:10.6023/A20030086

Acta Chimica Sinica ›› 2020, Vol. 78 ›› Issue (6): 490-503.DOI: 10.6023/A20030086 Previous Articles Next Articles

Review

细胞色素P450酶催化的烷烃选择性羟化

王曦翎^a, 陈杰^a,b, 马娜娜^a,b, 丛志奇^a,b

a 中国科学院青岛生物能源与过程研究所中国科学院生物燃料重点实验室山东省合成生物学重点实验室青岛 266101;
b 中国科学院大学北京 100049

投稿日期:2020-03-24 发布日期:2020-05-08
通讯作者: 丛志奇 E-mail:congzq@qibebt.ac.cn
作者简介:王曦翎,助理研究员,2016年于中国海洋大学医药学院获得医学博士学位,2016年7月至2019年8月在中国科学院青岛生物能源与过程研究所从事博士后研究.2019年9月起于中国科学院青岛生物能源与过程研究所工作.主要从事细胞色素P450酶的生物催化研究;丛志奇,研究员,博士生导师,2009年获得日本熊本大学理学博士学位.2009年至2016年,先后在日本分子科学研究所、名古屋大学从事科学研究工作.2016年05月加入中国科学院青岛生物能源与过程研究所,担任课题组长.2017年入选青岛市创新领军人才.从事金属酶的化学生物学与合成生物学研究,当前主要研究兴趣包括细胞色素P450酶的人工设计与实验室进化、甲烷和二氧化碳生物转化和非天然生物催化反应开发等.主持国家自然科学基金面上项目2项,中国科学院、青岛市和研究所自主部署项目等多项科研课题.
基金资助:
项目受国家自然科学基金（Nos.21778060，21977104）和青岛市创新领军人才计划（No.18-1-2-9-zhc）资助.

Selective Hydroxylation of Alkanes Catalyzed by Cytochrome P450 Enzymes

Wang Xiling^a, Chen Jie^a,b, Ma Nana^a,b, Cong Zhiqi^a,b

a CAS Key Laboratory of Biofuels, Shandong Provincial Key Laboratory of Synthetic Biology, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101;
b University of Chinese Academy of Sciences, Beijing 100049

Received:2020-03-24 Published:2020-05-08
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21778060, 21977104) and the Qingdao Innovative Leading Talent Project (No. 18-1-2-9-zhc).

The selective oxyfunctionalization of unactivated C-H bonds is one of long-standing issues and current topics in synthetic chemistry. One of the major synthetic targets for these reactions is the direct and selective hydroxylation of alkanes to alcohols, however, which faces many severe challenges in controlling chemoselectivity, regioselectivity and stereoselectivity. In nature, the oxidative metalloenzymes is capable of selectively catalyzing the insertion of oxygen into inert C-H bonds of alkanes, such as methane monooxygenases (MMO), soluble butane monooxygenases (sBMO), fungal peroxygenases and Cytochrome P450 monooxygenases (P450s). Among them, P450s that catalyze a variety of oxygenation reactions have attracted special attentions because of some intrinsic advantages. P450s are widely distributed in plants, animals and microorganisms and over 41000 sequences of P450 genes have been named from various databases, which enhances the potentials of P450s in developing the oxidative biocatalysts. In addition, compared with MMOs, P450s that have smaller molecule weight (≈45 kDa) are simple and amenable to recombinant expression and engineering. Herein, we reviewed the recent progress of alkanes hydroxylation by P450 enzymes either in its natural forms or engineered variants, as well as chemical activated systems. The related background and the catalytic mechanism of P450s for alkanes hydroxylation were firstly discussed. The representative examples by natural P450s mainly from CYP153, CYP52 and other P450 families were then outlined. The strategies of rational design and directed evolution on P450s engineering were then summarized focusing on the native/non-native alkane substrates. Three unusual strategies, including substrate engineering, decoy molecule, and dual-functional small molecule co-catalysis, were also discussed on their applications for activating P450s to hydroxylate non-native small alkanes. Finally, we perspective the challenges and solutions that faced by P450 enzymes in the development of new biocatalytic systems toward selective hydroxylation of alkanes. In conclusion, cytochrome P450 enzymes in both of their native and modified form are promising biocatalysts for alkanes hydroxylation and need further be investigated to gain the practical industrial applications.

Key words: alkane, enzyme catalysis, hydroxylation, cytochrome P450 enzyme, C-H activation, biocatalysis, oxidoreductases, directed evolution

Cite this article

Wang Xiling, Chen Jie, Ma Nana, Cong Zhiqi. Selective Hydroxylation of Alkanes Catalyzed by Cytochrome P450 Enzymes[J]. Acta Chimica Sinica, 2020, 78(6): 490-503.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Luo, Y. R. Handbook of Bond Dissociation Energies in Organic Compounds, Routledge, New York, 2003.
[2] Hashiguchi, B. G.; Konnick, M. M.; Bischof, S. M.; Gustafson, S. J.; Devarajan, D.; Gunsalus, N.; Daniel H.; Ess, D. H.; Periana, R. A. Science 2014, 343, 1232.
[3] Soussan, L.; Pen, N.; Belleville, M. P.; Marcano, J. S.; Jeanjean, D. P. J. Biotechnol. 2016, 222, 117.
[4] Sirajuddin, S.; Rosenzweig, A. C. Biochemistry 2015, 54, 2283.
[5] Cahalan, E.; Ernfors, M.; Müller, C.; Devaney, D.; Laughlin, R. J.; Watson, C. J.; Hennessy, D.; Grant, J.; Khalil, M. I.; McGeough, K. L.; Richards, K. G. Agric. Ecosyst. Environ. 2015, 199, 339.
[6] Van Beilen, J. B.; Wubbolts, M. G.; Witholt, B. Biodegradation 1994, 5, 161.
[7] Ortiz de Montellano, P. R. Cytochrome P450:Structure, Mechanism, and Biochemistry, Routledge, New York, 2005.
[8] (a) Urlacher, V. B.; Girhard, M. Trends Biotechnol. 2019, 37, 882.
(b) Wei, Y.; Ang, E. L.; Zhao, H. Curr. Opin. Chem. Biol. 2018, 43, 1.
(c) Jiang, Y.; Li, S. Chin. J. Org. Chem. 2018, 38, 2307(in Chinese). (蒋媛媛, 李盛英, 有机化学, 2018, 38, 2307).
(d) Cheng, Z.; Chen, P.; Liu, G. Acta Chim. Sinica 2019, 77, 856(in Chinese). (成忠明, 陈品红, 刘国生, 化学学报, 2019, 77, 856).
(e) Liu, Q.; Zhou, D.; Li, Z.; Luo, W.; Guo, C. Chin. J. Chem. 2017, 35, 1063.
(f) He, X.; Chen, L.; He, Q.; Xiao, H.; Zhou, X.; Ji, H. Chin. J. Chem. 2017, 35, 693.
(g) Lu, W.; Chen, X.; Feng, J.; Bao, Y.-J.; Wang, Y.; Wu, Q.; Zhu, D. Appl. Environ. Microbiol. 2018, 84, e00503-18.
[9] Paddon, C. J.; Westfall, P. J.; Pitera, D. J.; Benjamin, K.; Fisher, K.; McPhee, D.; Leavell, M. D.; Tai, A.; Main, A.; Eng, D.; Polichuk, D. R.; Teoh, K. H.; Reed, D. W.; Treynor, T.; Lenihan, J.; Fleck, M.; Bajad, S.; Dang, G.; Dengrove, D.; Diola, D.; Dorin, G.; Ellens, K. W.; Fickes, S.; Galazzo, J.; Gaucher, S. P.; Geistlinger, T.; Henry, R.; Hepp, M.; Horning, T.; Iqbal, T.; Jiang, H.; Kizer, L.; Lieu, B.; Melis, D.; Moss, N.; Regentin, R.; Secrest, S.; Tsuruta, H.; Vazquez, R.; Westblade, L. F.; Xu, L.; Yu, M.; Zhang, Y.; Zhao, L.; Lievense, J.; Covello, P. S.; Keasling, J. D.; Reiling, K. K.; Renninger, N. S.; Newman, J. D. Nature 2013, 496, 528.
[10] (a) Zhou, Q.; Luo, G.; Zhang, H.; Tang, G. Chin. J. Org. Chem. 2019, 39, 1169(in Chinese). (周强, 罗光彩, 张惠展, 唐功利, 有机化学, 2019, 39, 1169).
(b) Bai, X.; Guo, H.; Chen, D.; Yang, Q.; Tao, J.; Liu, W. Org. Chem. Front. 2020, 7, 584.
(c) Lv, J.-M.; Hu, D.; Gao, H.; Kushiro, T.; Awakawa, T.; Chen, G.-D.; Wang, C.-H.; Abe, I.; Yao, X.-S. Nat. Commun. 2017, 8, 1644.
[11] (a) Qi, F.; Lei, C.; Li, F.; Zhang, X.; Wang, J.; Zhang, W.; Fan, Z.; Li, W.; Tang, G.; Xiao, Y.; Zhao, G.; Li, S. Nat. Commun. 2018, 9, 2342.
(b) Sun, W.; Xue, H.; Liu, H.; Lv, B.; Yu, Y.; Wang, Y.; Huang, M.; Li, C. ACS Catal. 2020, 10, 4253.
(c) Tian, X.; Ruana, J.-X.; Huang, J.-Q.; Yang, C.-Q.; Fang, X.; Chen, Z.-W.; Hong, H.; Wang, L.-J.; Mao, Y.-B.; Lu, S.; Zhang, T.-Z.; Chen, X.-Y. Proc. Natl. Acad. Sci. U. S. A. 2018, 115, E5410.
(d) Wang, W.-F.; Xiao, H.; Zhong, J.-J. Biotechnol. Bioeng. 2018, 115, 1842.
[12] Coelho, P. S.; Brustad, E. M.; Kannan, A.; Arnold, F. H. Science 2013, 339, 307.
[13] 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.
[14] Kan, S.; Huang, X.; Gumulya, Y. Nature 2017, 552, 132.
[15] Haynes, C. A.; Gonzalez, R. Nat. Chem. Biol. 2014, 10, 331.
[16] Munz, D.; Strassner, T. Inorg. Chem. 2015, 54, 5043.
[17] Bordeaux, M.; Galarneau, A.; Drone, J. Angew. Chem., Int. Ed. 2012, 51, 10712.
[18] Lawton, T. J.; Rosenzweig, A. C. J. Am. Chem. Soc. 2016, 138, 9327.
[19] Nelson, D. R. Biochim. Biophys. Acta. Proteins Proteom. 2018, 1866, 141.
[20] (a) Poulos, T. L.; Finzel, B. C.; Howard, A. J. J. Mol. Biol. 1987, 195, 687.
(b) Tripathi, S.; Li, H.; Poulos, T. L. Science 2013, 340, 1227.
[21] Ravichandran, K. G.; Boddupalli, S. S.; Hasemann, C. A.; Peterson, J. A.; Deisenhofer, J. Science 1993, 261, 731.
[22] Haines, D. C.; Tomchick, D. R.; Machius, M.; Peterson, J. A. Biochemistry 2001, 40, 13456.
[23] (a) Rittle, J.; Green, M. T. Science 2010, 330, 933.
(b) Li, X.-X.; Postils, V.; Sun, W.; Faponle, A. S.; Solà, M.; Wang, Y.; Nam, W.; de Visser, S. P. Chem. Eur. J. 2017, 23, 6406.
[24] Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A. M.; Maves, S. A.; Benson, D. E.; Sweet, B. M.; Ringe, D.; Petsko, G. A.; Sligar, S. G. Science 2000, 287, 1615.
[25] Whitehouse, C. J.; Bell, S. G.; Wong, L. L. Chem. Soc. Rev. 2012, 41, 1218.
[26] Xu, F.; Bell, S. G.; Lednik, J.; Insley, A.; Rao, Z.; Wong, L. L. Angew. Chem., Int. Ed. 2005, 44, 4029.
[27] Fasan, R.; Chen, M. M.; Crook, N. C.; Arnold, F. H. Angew. Chem., Int. Ed. 2007, 46, 8414.
[28] Chen, J.; Kong, F.; Ma, N.; Zhao, P.; Liu, C.; Wang, X.; Cong, Z. ACS Catal. 2019, 9, 7350.
[29] (a) Scheps, D.; Malca, S. H.; Hoffmann, H.; Nestl, B. M.; Hauer, B. Org. Biomol. Chem. 2011, 9, 6727.
(b) Funhoff, E. G.; Bauer, U.; García-Rubio, I.; Witholt, B.; Van Beilen, J. B. J. Bacteriol. 2006, 5220.
(c) Bordeaux, M.; Girval, D.; Rullaud, R.; Subileau, M.; Dubreucq, E.; Drone, J. Appl. Microbiol. Biot. 2014, 98, 6275.
[30] (a) Hsieh, S.-C.; Wang, J.-H.; Lai, Y.-C.; Su, C.-Y.; Lee, K.-T. Appl. Environ. Microbiol. 2018, 84, e01806-17.
(b) Kochius, S.; Marwijk, J.; Ebrecht, A. C.; Opperman, D. J.; Smit, M. S. Catalysts 2018, 8, 531.
[31] Nie, Y.; Liang, J.-L.; Fang, H.; Tang, Y.-Q.; Wu, X.-L. Appl. Microbiol. Biotechnol. 2014, 98, 163.
[32] Zimmer, T.; Ohkuma, M.; Ohta, A.; Takagi, M.; Schunck, W. H. Biochem. Biophys. Res. Commun. 1996, 224, 784.
[33] Hanano, A.; Shaban, M.; Almousally, I.; Al-Ktaifani, M. Chemosphere 2015, 135, 418.
[34] Craft, D. L.; Madduri, K. M.; Eshoo, M.; Wilson, C. R. Appl. Environ. Microbiol. 2003, 5983.
[35] Van Bogaert, I. N. A.; Demey1, M.; Develter, D.; Soetaert, W.; Vandamme, E. J. FEMS Yeast Res. 2009, 9, 87.
[36] (a) Lida, T.; Sumita, T.; Ohta, A.; Takagi, M. Yeast 2000, 16, 1077.
(b) Panwar, S. L.; Krishnamurthy, S.; Gupta, V.; Alarco, A. M.; Raymond, M.; Sanglard, D.; Prasad, R. Yeast 2001, 18, 1117.
(c) Carratore, R. D.; Gervasi, P. G.; Contini, M. P.; Beffy, P.; Maserti, B. E.; Giovannetti, G.; Brondolo, A.; Longo, V. Biotechnol. Lett. 2011, 33, 1201.
[37] Trippe, K. M.; Wolpert, T. J.; Hyman, M. R.; Ciuffetti, L. M. Biodegradation 2014, 25, 137.
[38] Park, H.; Park, G.; Jeon, W.; Ahn, J.-O.; Yang, Y.-H.; Choi, K.-Y. Biotechnol. Adv. 2020, DOI:10.1016/j.biotechadv.2020.107504.
[39] (a) Von Bühler, C. J.; Urlacher, V. B. Chem. Commun. 2014, 50, 4089.
(b) Tieves, F.; Erenburg, I. N.; Mahmoud, O.; Urlacher, V. B. Biotechnol. Bioeng. 2016, 113, 1845.
[40] Syed, K.; Porollo, A.; Lam, Y. W. Appl. Environ. Microbiol. 2013, 79, 2692.
[41] (a) Greer, S.; Wen, M.; Bird, D.; Wu, X.; Samuels, L.; Kunst, L.; Jetter, R. Plant Physiol. 2007, 145, 653.
(b) Zhang, D.; Yang, H.; Wang, X.; Qiu, Y.; Tian, L.; Qi, X.; Qu, L. Q. New Phytol. 2020, 225, 2094.
[42] Minerdi, D.; Sadeghi, S. J.; Nardo, G. D.; Rua, F.; Castrignanò, S.; Allegra, P.; Gilardi, G. Mol. Microbiol. 2015, 95, 539.
[43] Fisher, M. B.; Zheng, Y. M.; Rettie, A. E. Biochem. Biophys. Res. Commun. 1998, 248, 352.
[44] (a) Maseme, M. J.; Pennec, A.; Marwijk, J.; Opperman, D. J.; Smit, M. S. Angew. Chem., Int. Ed. 2020, DOI:10.1002/anie. 202001055.
(b) Manning, J.; Tavanti, M.; Porter, J.; Kress, N.; De Visser, S.; Turner, N.; Flitsch, S. Angew. Chem., Int. Ed. 2019, 58, 5668.
(c) Sakai, K.; Matsuzaki, F.; Wise, L.; Sakai, Y.; Jindou, S.; Ichinose, H.; Takaya, N.; Kato, M.; Wariishi, H.; Shimizu, M. Appl. Environ. Microbiol. 2018, 84, e01091-18.
[45] (a) Johnston, J. B.; Kells, P. M.; Podust, L. M.; Ortiz de Montellano, P. R. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 20687.
(b) Salamanca, D.; Karande, R.; Schmid, A.; Dobslaw, D. Appl. Microbiol. Biotechnol. 2015, 99, 6889.
[46] (a) Yin, Y.-C.; Yu, H.-L.; Luan, Z.-J.; Li, R.-J.; Ouyang, P.-F.; Liu, J.; Xu, J.-H. ChemBioChem 2014, 15, 2443.
(b) Xie, L.; Chen, K.; Cui, H.; Wan, N.; Cui, B.; Han, W.; Chen, Y. ChemBioChem 2020, 20, DOI:10.1002/cbic.201900691.
[47] Bell, S. G.; Yang, W.; Dale, A.; Zhou, W.; Wong, L. L. Appl. Microbiol. Biotechnol. 2013, 97, 3979.
[48] Shoji, O.; Aiba, Y.; Watanabe, Y. Acc. Chem. Res. 2019, 52, 925.
[49] Dus, K.; Katagiri, M.; Yu, C. A.; Erbes, D. L.; Gunsalus, I. C. Biochem. Biophys. Res. Commun. 1970, 40, 1423.
[50] Stevenson, J. A.; Westlake, A. C. G.; Whittock, C.; Wong, L. L. J. Am. Chem. Soc. 1996, 118, 12846.
[51] Stevenson, J. A.; Bearpark, J. K.; Wong, L. L. New J. Chem. 1998, 22, 551.
[52] Bell, S. G.; Stevenson, J. A.; Boyd, H. D.; Campbell, S.; Riddle, A. D.; Orton, E. L.; Wong, L. L. Chem. Commun. 2002, 490.
[53] Bell, S. G.; Orton, E. L.; Boyd, H. D.; Stevenson, J. A.; Riddle, A. D.; Campbell, S.; Wong, L. L. Dalton Trans. 2003, 2133.
[54] Poulos, T. L.; Finzel, B. C.; Howard, A. J. Biochemistry 1986, 25, 5314.
[55] Miura, Y.; Fulco, A. J. Biochim. Biophys. Acta 1975, 388, 305.
[56] Adam, W.; Lukacs, Z.; Saha-Möller, C. R.; Weckerle, B.; Schreier, P. Eur. J. Org. Chem. 2000, 16, 2923.
[57] Appel, D.; Lutz, S.; Fischer, P.; Schwaneberg, U.; Schmid, R. D. J. Biotechnol. 2001, 88, 167.
[58] Glieder, A.; Farinas, E. T.; Arnold, F. H. Nat. Biotechnol. 2002, 20, 1135.
[59] Peters, M. W.; Meinhold, P.; Glieder, A.; Arnold, F. H. J. Am. Chem. Soc. 2003, 125, 13442.
[60] Meinhold, P.; Peters, M. W.; Chen, M. M.; Takahashi, K.; Arnold, F. H. ChemBioChem 2005, 6, 1765.
[61] Farinas, E. T.; Schwaneberg, U.; Gliede, A.; Arnold, F. H. Adv. Synth. Catal. 2001, 343, 601.
[62] Weber, E.; Seifert, A.; Antonovici, M.; Geinitz, C.; Pleiss, J.; Urlacher, V. B. Chem. Commun. 2011, 47, 944.
[63] Staudt, S.; Burda, E.; Giese, C.; Müller, C. A.; Marienhagen, J.; Schwaneberg, U.; Hummel, W.; Drauz, K.; Gröger, H. Angew. Chem., Int. Ed. 2013, 52, 2359.
[64] Müller, C. A.; Akkapurathu, B.; Winkler, T.; Svenja Staudt, S.; Hummel, W.; Gröger, H.; Schwaneberg, U. Adv. Synth. Catal. 2013, 355, 1787.
[65] Pennec, A.; Hoomann, F.; Smit, M. S.; Opperman, D. J. ChemCatChem 2015, 7, 236.
[66] Roiban, G. D.; Reetz, M. T. Chem. Commun. 2015, 51, 2208.
[67] Roiban, G. D.; Agudo, R.; Reetz, M. T. Angew. Chem., Int. Ed. 2014, 53, 8659.
[68] Zhang, W.; Tang, W.; Wang, Z.; Li, Z. Adv. Synth. Catal. 2010, 352, 3380.
[69] Chang, D. L.; Feiten, H. J.; Witholt, B.; Li, Z. Tetrahedron:Asymmetry 2002, 13, 2141.
[70] Chang, D. L.; Feiten, H. J.; Engesser, K. H.; Van Beilen, J. B.; Witholt, B.; Li, Z. Org. Lett. 2002, 4, 1859.
[71] Reetz, M. T. Angew. Chem., Int. Ed. 2011, 50, 138.
[72] Yang, Y.; Liu, J.; Li, Z. Angew. Chem., Int. Ed. 2014, 53, 3120.
[73] Landwehr, M.; Hochrein, L.; Otey, C. R.; Kasrayan, A.; Backvall, J. E.; Arnold, F. H. J. Am. Chem. Soc. 2006, 128, 6058.
[74] 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.
[75] Narayan, A. R. H.; Jiménez-Osés, G.; Liu, P.; Negretti, S.; Zhao, W.; Gilbert, M. M.; Ramabhadran, R. O., Yand, Y.-F.; Furan, L. R.; Li, Z.; Podust, L. M.; Montgomery, J.; Houk, K. N.; Sherman, D. H. Nat. Chem. 2015, 7, 653.
[76] Ma, N.; Chen, Z.; Chen, J.; Wang, C.; Zhou, H.; Yao, L.; Shoji, O.; Watanabe, Y.; Cong, Z. Angew. Chem., Int. Ed. 2018, 57, 7628.
[77] Xu, J.; Wang, C.; Cong, Z. Chem. Eur. J. 2019, 25, 6853.
[78] Shoji, O.; Yanagisawa, S.; Stanfield, J. K.; Suzuki, K.; Cong, Z.; Sugimoto, H.; Shiro, Y.; Watanabe, Y. Angew. Chem., Int. Ed. 2017, 56, 10324.
[79] Cong, Z.; Shoji, O.; Kasai, C.; Kawakami, N.; Sugimoto, H.; Shiro, Y.; Watanabe, Y. ACS Catal. 2015, 5, 150.
[80] Zhang, W.; Ma, M.; Hollmann, F. J. Am. Chem. Soc. 2019, 141, 3116.
[81] Demming, R. M.; Hammer, S. C.; Nestl, B. M.; Gergel, S.; Fademrecht, S.; Pleiss, J.; Hauer, B. Angew. Chem., Int. Ed. 2019, 58, 173.
[82] (a) Wang, Y.; Lan, D.; Durrani, R.; Hollmann, F. Curr. Opin. Chem. Biol. 2017, 37, 1.
(b) Piontek, K.; Strittmatter, E.; Ullrich, R.; Gröbe, G.; Pecyna, M. J.; Kluge, M.; Scheibner, K.; Hofrichter, M.; Plattner, D. A. J. Biol. Chem. 2013, 288, 34767.
[83] Wang, X.; Chen, J.; Chen, Z.; Zhou, H.; Cong, Z. Biotic Resources 2017, 39, 75(in Chinese). (王曦翎, 陈杰, 陈置丰, 周海峰, 丛志奇, 生物资源, 2017, 39, 75).
[84] Chen, Z.; Chen, J.; Ma, N.; Zhou, H.; Cong, Z. J. Porphyr. Phthalocya. 2018, 22, 831.
[85] Jiang, Y.; Wang, C.; Ma, N.; Chen, J.; Liu, C.; Wang, F.; Xu, J.; Cong, Z. Catal. Sci. Technol. 2020, 10, 1219.
[86] Kawakami, N.; Shoji, O.; Watanabe, Y. Angew. Chem., Int. Ed. 2011, 50, 5315.
[87] (a) Zilly, F. E.; Acevedo, J. P.; Augustyniak, W.; Deege, A.; Häusig, U. W.; Manfred, T.; Reetz, M. T. Angew. Chem., Int. Ed. 2011, 50, 2720.
(b) Zilly, F. E.; Acevedo, J. P.; Augustyniak, W.; Deege, A.; Häusig, U. W.; Manfred, T.; Reetz, M. T. Angew. Chem., Int. Ed. 2013, 52, 13503.
[88] Kawakami, N.; Shoji, O.; Watanabe, Y. Chem. Sci. 2013, 4, 2344.
[89] Ariyasu, S.; Kodama, Y.; Kasai, C.; Cong, Z.; Stanfield, J. K.; Aiba, Y.; Watanabe, Y.; Shoji, O. ChemCatChem 2019, 11, 4709.
[90] Kawakami, N.; Cong, Z.; Shoji, O.; Watanabe, Y. J. Porphyr. Phthalocya. 2015, 19, 329.
[91] Munday, S. D.; Shoji, O.; Watanabe, Y.; Wong, L. L.; Bell, S. G. Chem. Commun. 2016, 52, 1036.
[92] Peter, S.; Kinne, M.; Wang, X.; Ullrich, R.; Kayser, G.; Groves, J. T. FEBS J. 2011, 278, 3667.
[93] Cooley, R. B.; Dubbels, B. L.; Sayavedra-Soto, L. A.; Bottomley, P. J.; Arp, D. Microbiology 2009, 155, 2086.
[94] Chen, M.; Coelho, P. S.; Arnold, F. H. Adv. Synth. Catal. 2012, 354, 964.
[95] Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
[96] Lee, J. H.; Nam, D. H.; Lee, S. H.; Park, J. H.; Park, S. J.; Lee, S. H.; Park, C. B.; Jeong, K. J. Bioconjugate Chem. 2014, 25, 2101.
[97] Ge, J.; Lei, J.; Zare, R. N. Nat. Nanotechnol. 2012, 7, 428.
[98] Khatri, Y.; Hannemann, F.; Ewen, K. M.; Pistorius, D.; Perlova, O.; Kagawa, N.; Brachmann, A. O.; Müller, R.; Bernhardt, R. Chem. Biol. 2010, 17, 1295.
[99] Lee, J. H.; Nam, D. H.; Lee, S. H.; Park, J. H.; Park, C. B.; Jeong, K. J. J. Ind. Eng. Chem. 2016, 33, 28.
[100] Karande, R.; Schmid, A.; Buehler, K. Org. Process Res. Dev. 2016, 20, 361.

细胞色素P450酶催化的烷烃选择性羟化

Selective Hydroxylation of Alkanes Catalyzed by Cytochrome P450 Enzymes

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fengqin Gao, Yang Liu, Yinli Zhang, Yucheng Jiang. Study on Construction and Performance of Immobilized Enzyme Reactors by Carboxyl-functionalized Fe₃O₄ [J]. Acta Chimica Sinica, 2023, 81(4): 338-344.
[2]	Jianqiang Chen, Gangguo Zhu, Jie Wu. Recent Advances in Radical-Based Dehydroxylation of Hydroxyl Groups via Oxalates [J]. Acta Chimica Sinica, 2023, 81(11): 1609-1623.
[3]	Xia Gao, Huibin Pan, Zengxian He, Ke Yang, Chengfang Qiao, Yongliang Liu, Chunsheng Zhou. Construction and Structure-Activity Relationship of Immobilized Enzyme Reactor Based on Al-MOF-Derived Al₂O₃ with Hierarchical Structure [J]. Acta Chimica Sinica, 2021, 79(12): 1502-1510.
[4]	Zhao Ruinan, Hu Mancheng, Li Shuni, Zhai Quanguo, Jiang Yucheng. Immobilization of Chloroperoxidase in Metal Organic Framework and Its Catalytic Performance [J]. Acta Chim. Sinica, 2017, 75(3): 293-299.
[5]	Li Xinwei, Song Song, Jiao Ning. Oxidative Iodohydroxylation of Olefins with DMSO [J]. Acta Chim. Sinica, 2017, 75(12): 1202-1206.
[6]	Qi Lihua, Cai Wensheng, Shao Xueguang. Effect of Temperature on Near-infrared Spectra of n-Alkanes [J]. Acta Chim. Sinica, 2016, 74(2): 172-178.
[7]	Luo Feihua, Long Yang, Li Zhengkai, Zhou Xiangge. Palladium Catalyzed Arylation of C(sp³)-H Bonds of Carbonyl β-position in Water [J]. Acta Chim. Sinica, 2016, 74(10): 805-810.
[8]	Shang Xiaojie, Liu Zhongquan. Recent Advances in Free-Radical-Promoted Selective Activation of Alcohol/Ether α-O-C(sp³)-H Bond [J]. Acta Chimica Sinica, 2015, 73(12): 1275-1282.
[9]	Zhao Jinbo, Zhang Qian. Recent Advances in Directed Intramolecular C(sp³)-H Amination Reactions for the Construction of Aza-heterocycles [J]. Acta Chim. Sinica, 2015, 73(12): 1235-1244.
[10]	Liao Gang, Shi Bingfeng. Recent Advances on Transition-Metal-Catalyzed Halogenation of Unactivated C-H Bonds [J]. Acta Chimica Sinica, 2015, 73(12): 1283-1293.
[11]	Xu Jiabin, Chen Pinhong, Ye Jinxing, Liu Guosheng. Palladium-Catalyzed Trifluoromethylthiolation of Arenes via C-H Activation [J]. Acta Chimica Sinica, 2015, 73(12): 1294-1297.
[12]	Ding Zhengwei, Tan Qitao, Liu Bingxin, Zhang Kea, Xu Bin. Copper-Promoted Oxidative C-H Bond Amination of Hydrazones:Synthesis of 1H-Indazoles and 1H-Pyrazoles [J]. Acta Chim. Sinica, 2015, 73(12): 1302-1306.
[13]	Zhou Lihong, Lu Wenjun. Selective Functionalization of Normal Alkyl C-H Bonds Using Amides as Directing Groups [J]. Acta Chim. Sinica, 2015, 73(12): 1250-1274.
[14]	Lu Ping, Feng Chao, Loh Teck-Peng. Rh/Ag Bimetallic Catalyzed C-H Bond Olefination of Benzonitriles [J]. Acta Chim. Sinica, 2015, 73(12): 1315-1319.
[15]	Wang Yuhui, Cao Zhongyan, Niu Yanfei, Zhao Xiaoli, Zhou Jian. Highly Enantioselective Organocatalytic aza-Henry Reaction of Nitroalkanes to N-Boc Isatin Ketimines [J]. Acta Chimica Sinica, 2014, 72(7): 867-872.