SIOC 中文
ACS
Adv search

Acta Chimica Sinica >

2020 , Vol. 78 >Issue 6: 490 - 503

DOI: https://doi.org/10.6023/A20030086

Review

Selective Hydroxylation of Alkanes Catalyzed by Cytochrome P450 Enzymes

  • Wang Xiling ,
  • Chen Jie ,
  • Ma Nana ,
  • Cong Zhiqi
Expand
  • 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 date: 2020-03-24

  Online 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).

Fold

Abstract

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 . DOI: 10.6023/A20030086

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.
Options
Outlines

/

〈 〉