Abstract
Site-specific protein conjugation is a critical step in the generation of unique protein analogs for a range of basic research and therapeutic developments. Protein transformations must target a precise residue in the presence of a plethora of functional groups to obtain a well-characterized homogeneous product. Competing reactive residues on natural proteins render rapid and selective conjugation a challenging task. Organometallic reagents have recently emerged as a powerful strategy to achieve site-specific labeling of a diverse set of biopolymers, due to advances in water-soluble ligand design, high reaction rate, and selectivity. The thiophilic nature of various transition metals, especially soft metals, makes cysteine an ideal target for these reagents. The distinctive reactivity and selectivity of organometallic-based reactions, along with the unique reactivity and abundancy of cysteine within the human proteome, provide a powerful platform to modify native proteins in aqueous media. These reactions often provide the modified proteins with a stable linkage made from irreversible cross-coupling steps. Additionally, transition metal reagents have recently been applied for the decaging of cysteine residues in the context of chemical protein synthesis. Orthogonal cysteine protecting groups and functional tags are often necessary for the synthesis of challenging proteins, and organometallic reagents are powerful tools for selective, rapid, and water-compatible removal of those moieties. This review examines transition metal-based reactions of cysteine residues for the synthesis and modification of natural peptides and proteins.
Acknowledgments
I am truly grateful to Prof. Ashraf Brik for supervision and support during my graduate studies at the Technion-Israel Institute of Technology. I would also like to thank Prof. Bradley L. Pentelute for the opportunity to conduct my postdoctoral training in his lab and Prof. Stephen L. Buchwald for the opportunity to collaborate during this period. Dr. Christopher R. Shugrue and Dr. Sebastian Pompuln are acknowledged for providing input and advice during the preparation of this manuscript. M.J. is currently the recipient of the Fulbright and Rothschild Postdoctoral Fellowships at MIT. The Israel Council for Higher Education is gratefully acknowledged for the VATAT postdoctoral scholarship.
References
[1] C. T. Walsh, S. Garneau-Tsodikova, G. J. Gatto. Angew. Chemie Int. Ed. (2005), https://doi.org/10.1002/anie.200501023.Search in Google Scholar PubMed
[2] N. Krall, F. P. Da Cruz, O. Boutureira, G. J. L. Bernardes. Nat. Chem. (2016), https://doi.org/10.1038/nchem.2393.Search in Google Scholar PubMed
[3] C. D. Spicer, B. G. Davis. Nat. Commun. (2014), https://doi.org/10.1038/ncomms5740.Search in Google Scholar PubMed
[4] O. Boutureira, G. J. L. Bernardes. Chem. Rev. (2015), https://doi.org/10.1021/cr500399p.Search in Google Scholar PubMed
[5] I. Dovgan, O. Koniev, S. Kolodych, A. Wagner. Bioconjug. Chem. (2019), https://doi.org/10.1021/acs.bioconjchem.9b00306.Search in Google Scholar PubMed
[6] T. Macculloch, A. Buchberger, N. Stephanopoulos. Org. Biomol. Chem. (2019), https://doi.org/10.1039/c8ob02436g.Search in Google Scholar PubMed
[7] K. Wang, A. Sachdeva, D. J. Cox, N. W. Wilf, K. Lang, S. Wallace, R. A. Mehl, J. W. Chin. Nat. Chem. (2014), https://doi.org/10.1038/nchem.1919.Search in Google Scholar PubMed PubMed Central
[8] N. Nischan, C. P. R. Hackenberger. J. Org. Chem. (2014), https://doi.org/10.1021/jo502136n.Search in Google Scholar PubMed
[9] E. L. Sievers, P. D. Senter. Annu. Rev. Med. (2013), https://doi.org/10.1146/annurev-med-050311-201823.Search in Google Scholar PubMed
[10] T. Rodrigues, G. J. L. Bernardes. Angew. Chemie Int. Ed. (2018), https://doi.org/10.1002/anie.201712185.Search in Google Scholar PubMed PubMed Central
[11] T. O. Yeates, S. B. H. Kent. Annu. Rev. Biophys. (2012), https://doi.org/10.1146/annurev-biophys-050511-102333.Search in Google Scholar PubMed
[12] M. Jbara, H. Sun, G. Kamnesky, A. Brik. Curr. Opin. Chem. Biol. (2018), https://doi.org/10.1016/j.cbpa.2018.02.001.Search in Google Scholar PubMed
[13] J. A. Shadish, C. A. DeForest. Matter (2020), https://doi.org/10.1016/j.matt.2019.11.011.Search in Google Scholar
[14] C. H. Jun. Chem. Soc. Rev. (2004), https://doi.org/10.1039/b308864m.Search in Google Scholar PubMed
[15] P. G. Isenegger, B. G. Davis. J. Am. Chem. Soc. (2019), https://doi.org/10.1021/jacs.8b13187.Search in Google Scholar PubMed PubMed Central
[16] J. Ohata, S. C. Martin, Z. T. Ball. Angew. Chemie Int. Ed. (2019), https://doi.org/10.1002/anie.201807536.Search in Google Scholar PubMed
[17] J. M. Antos, M. B. Francis. Curr. Opin. Chem. Biol. (2006), https://doi.org/10.1016/j.cbpa.2006.04.009.Search in Google Scholar PubMed
[18] E. Defrancq, S. Messaoudi. ChemBioChem (2017), https://doi.org/10.1002/cbic.201600599.Search in Google Scholar PubMed
[19] M. Jbara, S. K. Maity, A. Brik. Angew. Chemie Int. Ed. (2017), https://doi.org/10.1002/anie.201702370.Search in Google Scholar PubMed
[20] S. V. Chankeshwara, E. Indrigo, M. Bradley. Curr. Opin. Chem. Biol. (2014), https://doi.org/10.1016/j.cbpa.2014.07.007.Search in Google Scholar PubMed
[21] E. V. Vinogradova. Pure Appl. Chem. (2017), https://doi.org/10.1515/pac-2017-0207.Search in Google Scholar
[22] L. R. Malins. Curr. Opin. Chem. Biol. (2018), https://doi.org/10.1016/j.cbpa.2018.03.019.Search in Google Scholar PubMed
[23] K. Lang, J. W. Chin. Chem. Rev. (2014), https://doi.org/10.1021/cr400355w.Search in Google Scholar PubMed
[24] J. M. Chalker, G. J. L. Bernardes, B. G. Davis. Acc. Chem. Res. (2011), https://doi.org/10.1021/ar200056q.Search in Google Scholar PubMed
[25] E. A. Hoyt, P. M. S. D. Cal, B. L. Oliveira, G. J. L. Bernardes. Nat. Rev. Chem. (2019), https://doi.org/10.1038/s41570-019-0079-1.Search in Google Scholar
[26] J. N. DeGruyter, L. R. Malins, P. S. Baran. Biochemistry (2017), https://doi.org/10.1021/acs.biochem.7b00536.Search in Google Scholar PubMed PubMed Central
[27] J. M. Chalker, G. J. L. Bernardes, Y. A. Lin, B. G. Davis. Chem. An Asian J. (2009), https://doi.org/10.1002/asia.200800427.Search in Google Scholar PubMed
[28] S. B. Gunnoo, A. Madder. ChemBioChem (2016), https://doi.org/10.1002/cbic.201500667.Search in Google Scholar PubMed
[29] J. M. Chalker, S. B. Gunnoo, O. Boutureira, S. C. Gerstberger, M. Fernández-González, G. J. L. Bernardes, L. Griffin, H. Hailu, C. J. Schofield, B. G. Davis. Chem. Sci. (2011), https://doi.org/10.1039/c1sc00185j.Search in Google Scholar
[30] C. Zhang, E. V. Vinogradova, A. M. Spokoyny, S. L. Buchwald, B. L. Pentelute. Angew. Chemie Int. Ed. (2019), https://doi.org/10.1002/anie.201806009.Search in Google Scholar PubMed PubMed Central
[31] P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent. Science (1994), https://doi.org/10.1126/science.7973629.Search in Google Scholar PubMed
[32] S. B. H. Kent. Chem. Soc. Rev. (2009), https://doi.org/10.1039/b700141j.Search in Google Scholar PubMed
[33] S. Bondalapati, M. Jbara, A. Brik. Nat. Chem. (2016), https://doi.org/10.1038/nchem.2476.Search in Google Scholar PubMed
[34] S. S. Kulkarni, J. Sayers, B. Premdjee, R. J. Payne. Nat. Rev. Chem. (2018), https://doi.org/10.1038/s41570-018-0122.Search in Google Scholar
[35] V. Agouridas, O. El Mahdi, V. Diemer, M. Cargoët, J. C. M. Monbaliu, O. Melnyk. Chem. Rev. (2019), https://doi.org/10.1021/acs.chemrev.8b00712.Search in Google Scholar PubMed
[36] M. Holt, T. Muir. Annu. Rev. Biochem. (2015), https://doi.org/10.1146/annurev-biochem-060614-034429.Search in Google Scholar PubMed PubMed Central
[37] A. C. Conibear, E. E. Watson, R. J. Payne, C. F. W. Becker. Chem. Soc. Rev. (2018), https://doi.org/10.1039/c8cs00573g.Search in Google Scholar PubMed
[38] S. K. Maity, M. Jbara, A. Brik. J. Pept. Sci. (2016), https://doi.org/10.1002/psc.2848.Search in Google Scholar PubMed
[39] P. Bisseret, H. Abdelkafi, N. Blanchard. Chem. Sci. (2018), https://doi.org/10.1039/c8sc00780b.Search in Google Scholar PubMed PubMed Central
[40] W. M. Cheng, X. Lu, J. Shi, L. Liu. Org. Chem. Front. (2018), https://doi.org/10.1039/c8qo00765a.Search in Google Scholar
[41] L. R. Malins. Aust. J. Chem. (2016), https://doi.org/10.1071/CH16416.Search in Google Scholar
[42] H. Dibowski, F. P. Schmidtchen. Angew. Chemie Int. Ed. (1998), https://doi.org/10.1002/(SICI)1521-3773(19980302)37:4<476::AID-ANIE476>3.0.CO;2-2.Search in Google Scholar
[43] E. V. Vinogradova, C. Zhang, A. M. Spokoyny, B. L. Pentelute, S. L. Buchwald. Nature (2015), https://doi.org/10.1038/nature15739.Search in Google Scholar PubMed PubMed Central
[44] A. J. Rojas, B. L. Pentelute, S. L. Buchwald. Org. Lett. (2017), https://doi.org/10.1021/acs.orglett.7b01911.Search in Google Scholar PubMed PubMed Central
[45] A. J. Rojas, C. Zhang, E. V. Vinogradova, N. H. Buchwald, J. Reilly, B. L. Pentelute, S. L. Buchwald. Chem. Sci. (2017), https://doi.org/10.1039/c6sc05454d.Search in Google Scholar PubMed PubMed Central
[46] W. Zhao, H. G. Lee, S. L. Buchwald, J. M. Hooker. J. Am. Chem. Soc. (2017), https://doi.org/10.1021/jacs.7b02761.Search in Google Scholar PubMed PubMed Central
[47] K. Kubota, P. Dai, B. L. Pentelute, S. L. Buchwald. J. Am. Chem. Soc. (2018), https://doi.org/10.1021/jacs.8b00172.Search in Google Scholar PubMed PubMed Central
[48] H. H. Dhanjee, S. Azin, I. Buslov, A. R. Loftis, S. L. Buchwald, B. L. Pentelute. J. Am. Chem. Soc. (2020), https://doi.org/10.1021/jacs.0c03143.Search in Google Scholar PubMed PubMed Central
[49] R. A. A. Al-Shuaeeb, S. Kolodych, O. Koniev, S. Delacroix, S. Erb, S. Nicolaÿ, J. C. Cintrat, J. D. Brion, S. Cianférani, M. Alami, A. Wagner, M. Messaouddi. Chem. A Eur. J. (2016), https://doi.org/10.1002/chem.201602277.Search in Google Scholar PubMed
[50] J. Willwacher, R. Raj, S. Mohammed, B. G. Davis. J. Am. Chem. Soc. (2016), https://doi.org/10.1021/jacs.6b04043.Search in Google Scholar PubMed
[51] J. M. Chalker, C. S. C. Wood, B. G. Davis. J. Am. Chem. Soc. (2009), https://doi.org/10.1021/ja907150m.Search in Google Scholar PubMed
[52] M. K. Bilyard, H. J. Bailey, L. Raich, M. A. Gafitescu, T. Machida, J. Iglésias-Fernández, S. S. Lee, C. D. Spicer, C. Rovira, W. W. Yue, B. G. Davis. Nature (2018), https://doi.org/10.1038/s41586-018-0644-7.Search in Google Scholar PubMed
[53] A. S. K. Hashmi. Chem. Rev. (2007), https://doi.org/10.1021/cr000436x.Search in Google Scholar PubMed
[54] Z. Li, C. Brouwer, C. He. Chem. Rev. (2008), https://doi.org/10.1021/cr068434l.Search in Google Scholar PubMed
[55] K. K. Y. Kung, H. M. Ko, J. F. Cui, H. C. Chong, Y. C. Leung, M. K. Wong. Chem. Commun. (2014), https://doi.org/10.1039/c4cc04467c.Search in Google Scholar PubMed
[56] M. S. Messina, J. M. Stauber, M. A. Waddington, A. L. Rheingold, H. D. Maynard, A. M. Spokoyny. J. Am. Chem. Soc. (2018), https://doi.org/10.1021/jacs.8b04115.Search in Google Scholar PubMed PubMed Central
[57] B. A. Vara, X. Li, S. Berritt, C. R. Walters, E. J. Petersson, G. A. Molander. Chem. Sci. (2018), https://doi.org/10.1039/c7sc04292b.Search in Google Scholar PubMed PubMed Central
[58] K. Hanaya, J. Ohata, M. K. Miller, A. E. Mangubat-Medina, M. J. Swierczynski, D. C. Yang, R. M. Rosenthal, B. V. Popp, Z. T. Ball. Chem. Commun. (2019), https://doi.org/10.1039/c9cc00159j.Search in Google Scholar PubMed
[59] T. Schlatzer, J. Kriegesmann, H. Schröder, M. Trobe, C. Lembacher-Fadum, S. Santner, A. V. Kravchuk, C. F. W. Becker, R. Breinbauer. J. Am. Chem. Soc. (2019), https://doi.org/10.1021/jacs.9b08279.Search in Google Scholar PubMed PubMed Central
[60] A. On-Yee Chan, J. Lui-Lui Tsai, V. Kar-Yan Lo, G. L. Li, M. K. Wong, C. M. Che. Chem. Commun. (2013), https://doi.org/10.1039/c2cc38214h.Search in Google Scholar PubMed
[61] R. Kundu, Z. T. Ball. Chem. Commun. (2013), https://doi.org/10.1039/c2cc37323h.Search in Google Scholar PubMed
[62] B. M. Trost, M. L. Crawley. Chem. Rev. (2003), https://doi.org/10.1021/cr020027w.Search in Google Scholar PubMed
[63] S. D. Tilley, M. B. Francis. J. Am. Chem. Soc. (2006), https://doi.org/10.1021/ja057106k.Search in Google Scholar PubMed
[64] J. M. Antos, M. B. Francis. J. Am. Chem. Soc. (2004), https://doi.org/10.1021/ja047272c.Search in Google Scholar PubMed
[65] C. P. R. Hackenberger, D. Schwarzer. Angew. Chemie Int. Ed. (2008), https://doi.org/10.1002/anie.200801313.Search in Google Scholar PubMed
[66] V. R. Pattabiraman, J. W. Bode. Nature (2011), https://doi.org/10.1038/nature10702.Search in Google Scholar PubMed
[67] L. Raibaut, N. Ollivier, O. Melnyk. Chem. Soc. Rev. (2012), https://doi.org/10.1039/c2cs35147a.Search in Google Scholar PubMed
[68] S. Nadal, R. Raj, S. Mohammed, B. G. Davis. Curr. Opin. Chem. Biol. (2018), https://doi.org/10.1016/j.cbpa.2018.02.004.Search in Google Scholar PubMed
[69] C. J. A. Leonen, E. Upadhyay, C. Chatterjee. Curr. Opin. Chem. Biol. (2018), https://doi.org/10.1016/j.cbpa.2018.02.005.Search in Google Scholar PubMed PubMed Central
[70] M. Morgan, Jbara, M., Brik, A., Wolberger, C., Methods Enzymol. (2019), https://doi.org/10.1016/bs.mie.2019.01.003.Search in Google Scholar PubMed PubMed Central
[71] S. B. Kent. Curr. Opin. Chem. Biol. (2018), https://doi.org/10.1016/j.cbpa.2018.03.012.Search in Google Scholar PubMed
[72] H. Derakhshankhah, S. Jafari. Biomed. Pharmacother. (2018), https://doi.org/10.1016/j.biopha.2018.09.097.Search in Google Scholar PubMed
[73] P. E. Dawson, S. B. H. Kent. Annu. Rev. Biochem. (2000), https://doi.org/10.1146/annurev.biochem.69.1.923.Search in Google Scholar PubMed
[74] J. W. Bode, R. M. Fox, K. D. Baucom. Angew. Chemie Int. Ed. (2006), https://doi.org/10.1002/anie.200503991.Search in Google Scholar PubMed
[75] I. Pusterla, J. W. Bode. Nat. Chem. (2015), https://doi.org/10.1038/nchem.2282.Search in Google Scholar PubMed
[76] Y. Zhang, C. Xu, H. Y. Lam, C. L. Lee, X. Li. Proc. Natl. Acad. Sci. U. S. A. (2013), https://doi.org/10.1073/pnas.1221012110.Search in Google Scholar PubMed PubMed Central
[77] C. L. Lee, X. Li. Curr. Opin. Chem. Biol. (2014), https://doi.org/10.1016/j.cbpa.2014.09.023.Search in Google Scholar PubMed
[78] N. J. Mitchell, L. R. Malins, X. Liu, R. E. Thompson, B. Chan, L. Radom, R. J. Payne. J. Am. Chem. Soc. (2015), https://doi.org/10.1021/jacs.5b07237.Search in Google Scholar PubMed
[79] T. S. Chisholm, S. S. Kulkarni, K. R. Hossain, F. Cornelius, R. J. Clarke, R. J. Payne. J. Am. Chem. Soc. (2020), https://doi.org/10.1021/jacs.9b12558.Search in Google Scholar PubMed
[80] A. Isidro-Llobet, M. Álvarez, F. Albericio. Chem. Rev. (2009), https://doi.org/10.1021/cr800323s.Search in Google Scholar PubMed
[81] S. K. Maity, M. Jbara, G. Mann, G. Kamnesky, A. Brik. Nat. Protoc. (2017), https://doi.org/10.1038/nprot.2017.049.Search in Google Scholar PubMed
[82] H. Kunz, H. Waldmann. Angew. Chemie Int. Ed. English (1984), https://doi.org/10.1002/anie.198400711.Search in Google Scholar
[83] M. Jbara, S. K. Maity, M. Seenaiah, A. Brik. J. Am. Chem. Soc. (2016), https://doi.org/10.1021/jacs.5b13580.Search in Google Scholar PubMed
[84] Z. Zhao, N. Metanis. Angew. Chemie Int. Ed. (2019), https://doi.org/10.1002/anie.201909484.Search in Google Scholar PubMed
[85] N. Naruse, D. Kobayashi, K. Ohkawachi, A. Shigenaga, A. Otaka. J. Org. Chem. (2020), https://doi.org/10.1021/acs.joc.9b02388.Search in Google Scholar PubMed
[86] S. K. Maity, M. Jbara, S. Laps, A. Brik. Angew. Chemie Int. Ed. (2016), https://doi.org/10.1002/anie.201603169.Search in Google Scholar PubMed
[87] M. Jbara, S. Laps, M. Morgan, G. Kamnesky, G. Mann, C. Wolberger, A. Brik. Nat. Commun. (2018), https://doi.org/10.1038/s41467-018-05628-0.Search in Google Scholar PubMed PubMed Central
[88] J. J. Ling, C. Fan, H. Qin, M. Wang, J. Chen, P. Wittung-Stafshede, T. F. Zhu. Angew. Chemie Int. Ed. (2020), https://doi.org/10.1002/anie.201914799.Search in Google Scholar PubMed PubMed Central
[89] M. Jbara, N. Guttmann-Raviv, S. K. Maity, N. Ayoub, A. Brik. Bioorganic Med. Chem. (2017), https://doi.org/10.1016/j.bmc.2017.04.015.Search in Google Scholar PubMed
[90] N. Kamo, G. Hayashi, A. Okamoto. Org. Lett. (2019), https://doi.org/10.1021/acs.orglett.9b03152.Search in Google Scholar PubMed
[91] M. Jbara, S. K. Maity, A. Brik. European J. Org. Chem. (2019), https://doi.org/10.1002/ejoc.201900257.Search in Google Scholar
[92] X. L. Tan, M. Pan, Y. Zheng, S. Gao, L. J. Liang, Y. M. Li. Chem. Sci. (2017), https://doi.org/10.1039/c7sc02937c.Search in Google Scholar PubMed PubMed Central
[93] S. Bondalapati, E. Eid, S. M. Mali, C. Wolberger, A. Brik. Chem. Sci. (2017), https://doi.org/10.1039/c7sc00488e.Search in Google Scholar PubMed PubMed Central
[94] G. C. Chu, M. Pan, J. Li, S. Liu, C. Zuo, Z. Bin Tong, J. S. Bai, Q. Gong, H. Ai, J. Fan, X. Meng, Y.-C. Huang, J. Shi, H. Deng, C. Tian, Y.-M. Li, L. Liu. J. Am. Chem. Soc. (2019), https://doi.org/10.1021/jacs.8b13213.Search in Google Scholar PubMed
[95] M. Nune, M. T. Morgan, Z. Connell, L. McCullough, M. Jbara, H. Sun, A. Brik, T. Formosa, C. Wolberger. Elife (2019), https://doi.org/10.7554/eLife.40988.Search in Google Scholar PubMed PubMed Central
[96] H. Sun, S. M. Mali, S. K. Singh, R. Meledin, A. Brik, Y. T. Kwon, Y. Kravtsova-Ivantsiv, B. Bercovich, A. Ciechanover. Proc. Natl. Acad. Sci. U. S. A. (2019), https://doi.org/10.1073/pnas.1822148116.Search in Google Scholar PubMed PubMed Central
[97] S. Laps, H. Sun, G. Kamnesky, A. Brik. Angew. Chemie Int. Ed. (2019), https://doi.org/10.1002/anie.201900988.Search in Google Scholar PubMed
[98] T. D. Kondasinghe, H. Y. Saraha, S. B. Odeesho, J. L. Stockdill. Org. Biomol. Chem. (2017), https://doi.org/10.1039/c7ob00536a.Search in Google Scholar PubMed PubMed Central
[99] J. Liu, R. Cheng, H. Wu, S. Li, P. G. Wang, W. F. DeGrado, S. Rozovsky, L. Wang. Angew. Chemie Int. Ed. (2018), https://doi.org/10.1002/anie.201806197.Search in Google Scholar PubMed PubMed Central
[100] M. P. Exner, T. Kuenzl, T. M. T. To, Z. Ouyang, S. Schwagerus, M. G. Hoesl, C. P. R. Hackenberger, M. C. Lensen, S. Panke, N. Budisa. ChemBioChem (2017), https://doi.org/10.1002/cbic.201600537.Search in Google Scholar PubMed
[101] N. Kamo, G. Hayashi, A. Okamoto. Angew. Chemie Int. Ed. (2018), https://doi.org/10.1002/anie.201809765.Search in Google Scholar PubMed
[102] M. Jbara, S. Laps, S. K. Maity, A. Brik. Chem. - A Eur. J. (2016), https://doi.org/10.1002/chem.201603676.Search in Google Scholar PubMed
[103] G. Mann, G. Satish, R. Meledin, G. B. Vamisetti, A. Brik. Angew. Chemie Int. Ed. (2019), https://doi.org/10.1002/anie.201906545.Search in Google Scholar PubMed
[104] S. K. Maity, G. Mann, M. Jbara, S. Laps, G. Kamnesky, A. Brik. Org. Lett. (2016), https://doi.org/10.1021/acs.orglett.6b01442.Search in Google Scholar PubMed
[105] M. Jbara, E. Eid, A. Brik. J. Am. Chem. Soc. (2020), https://doi.org/10.1021/jacs.9b13216.Search in Google Scholar PubMed
[106] J. M. Antos, J. M. McFarland, A. T. Iavarone, M. B. Francis. J. Am. Chem. Soc. (2009), https://doi.org/10.1021/ja900094h.Search in Google Scholar PubMed PubMed Central
[107] D. T. Cohen, C. Zhang, B. L. Pentelute, S. L. Buchwald. J. Am. Chem. Soc. (2015), https://doi.org/10.1021/jacs.5b05447.Search in Google Scholar PubMed PubMed Central
[108] J. Liu, F. Zheng, R. Cheng, S. Li, S. Rozovsky, Q. Wang, L. Wang. J. Am. Chem. Soc. (2018), https://doi.org/10.1021/jacs.8b04603.Search in Google Scholar PubMed PubMed Central
[109] J. Li, J. Yu, J. Zhao, J. Wang, S. Zheng, S. Lin, L. Chen, M. Yang, S. Jia, X. Zhang, P. R. Chen. Nat. Chem. (2014), https://doi.org/10.1038/nchem.1887.Search in Google Scholar PubMed
[110] M. Jbara, E. Eid, A. Brik. Org. Biomol. Chem. (2018), https://doi.org/10.1039/c8ob00890f.Search in Google Scholar PubMed
[111] N. Kamo, G. Hayashi, A. Okamoto. Chem. Commun. (2018), https://doi.org/10.1039/c8cc01965g.Search in Google Scholar PubMed
[112] J. Wang, S. Zheng, Y. Liu, Z. Zhang, Z. Lin, J. Li, G. Zhang, X. Wang, J. Li, P. R. Chen, J. Am. Chem. Soc. (2016), https://doi.org/10.1021/jacs.6b08933.Search in Google Scholar PubMed
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