Citation: Fang Ge-Min, Chen Xiao-Xu, Yang Qian-Qian, Zhu Liang-Jing, Li Ning-Ning, Yu Hai-Zhu, Meng Xiang-Ming. Discovery, structure, and chemical synthesis of disulfide-rich peptide toxins and their analogs[J]. Chinese Chemical Letters, ;2018, 29(7): 1033-1042. doi: 10.1016/j.cclet.2018.02.002 shu

Discovery, structure, and chemical synthesis of disulfide-rich peptide toxins and their analogs

a.
Institute of Physical Science and Information Technology, Anhui University, Hefei 230601, China
b.
Department of Chemistry, Anhui University, Hefei 230601, China

Corresponding author: Fang Ge-Min, fgmsxy@gmail.com Meng Xiang-Ming, mengxm@ahu.edu.cn
Received Date: 28 November 2017
Revised Date: 22 January 2018
Accepted Date: 25 January 2018
Available Online: 5 July 2018

Figures(11)

Recently, medicinal peptide molecules are of great interest to many international pharmaceutical companies, mainly because of their relatively lower research costs, shorter research cycles, and the greater likelihood of being drugs, when compared with traditional small molecules. Due to the great variety in molecule structures and the diverse biological functions, disulfide-rich peptide toxins have become a shining molecular library for the development of polypeptide drugs. In view of the increasing amount of related publications, here we summarize the discovery, structural elucidation and chemical synthesis of disulfide-rich peptide toxins and their analogs.
- Peptide toxins,
- Conotoxins,
- Cyclotides,
- Disulfide mimics,
- Chemical synthesis
1. [1]
  K. Fosgerau, T. Hoffamnn, Drug Discov. Today 20(2015) 122-128. doi: 10.1016/j.drudis.2014.10.003
2. [2]
  B.B. Carstens, G. Berecki, J.T. Daniel, et al., Angew. Chem. Int. Ed. 55(2016) 4692-4696. doi: 10.1002/anie.201600297
3. [3]
  T. Durek, I. Vetter, C.I.A. Wang, et al., ACS Chem. Biol. 8(2013) 1215-1222. doi: 10.1021/cb400012k
4. [4]
  H. Zhang, M. Du, J. Xie, et al., Angew. Chem. Int. Ed. 55(2016) 9306-9310. doi: 10.1002/anie.201603052
5. [5]
  C. Heinis, T. Rutherford, S. Freund, G. Winter, Nat. Chem. Biol. 5(2009) 502-507. doi: 10.1038/nchembio.184
6. [6]
  T. Passioura, T. Katoh, Y. Goto, H. Suga, Annu. Rev. Biochem. 83(2014) 727-752. doi: 10.1146/annurev-biochem-060713-035456
7. [7]
  Y. Li, A. Gould, T. Aboye, et al., J. Med. Chem. 60(2017) 1916-1927. doi: 10.1021/acs.jmedchem.6b01689
8. [8]
  K. Jagadish, A. Gould, R. Borra, et al., Angew. Chem. Int. Ed. 54(2015) 8390-8394. doi: 10.1002/anie.201501186
9. [9]
  J.G. McGivern, Neuropsychiatr. Dis. Treat. 3(2007) 69-85. doi: 10.2147/nedt.2007.3.issue-1
10. [10]
  S.W.B. Yu, S.S.C. Rao, Therap. Adv. Gastroenterol. 7(2014) 193-205. doi: 10.1177/1756283X14537882
11. [11]
  R.H. Thomas, D.R. Luthin, Pharmacotherapy 35(2015) 613-630. doi: 10.1002/phar.2015.35.issue-6
12. [12]
  K.B. Akondi, M. Muttenthaler, S. Dutertre, et al., Chem. Rev.114(2014) 5815-5847. doi: 10.1021/cr400401e
13. [13]
  A.C. Conibear, D.J. Craik, Angew. Chem. Int. Ed. 53(2014) 10612-10623. doi: 10.1002/anie.201402167
14. [14]
  B.M. Olivera, W.R. Gray, R. Zeikus, et al., Science 230(1985) 1338-1343. doi: 10.1126/science.4071055
15. [15]
  R.A. Myers, L.J.L. Cruz, J.E. Rivier, B.M. Olivera, Chem. Rev. 93(1993) 1923-1936. doi: 10.1021/cr00021a013
16. [16]
  A.G. Craig, J. Toxicol. Toxin Rev. 19(2000) 53-93. doi: 10.1081/TXR-100100315
17. [17]
  B.M. Ueberheide, D. Fenyö, P.F. Alewood, B.T. Chait, Proc. Natl. Acad. Sci. U. S. A. 106(2009) 6910-6915. doi: 10.1073/pnas.0900745106
18. [18]
  Q.Y. He, Q.Z. He, X.C. Deng, et al., Nucleic Acids Res. 36(2008) D293-297.
19. [19]
  G. Naamati, M. Askenazi, M. Linial, Nucleic Acids Res. 37(2009) W363-368. doi: 10.1093/nar/gkp299
20. [20]
  E. Lim, A. Pon, Y. Djoumbou, et al., Nucleic Acids Res. 38(2010) D781-786. doi: 10.1093/nar/gkp934
21. [21]
  Q. Kaas, R. Yu, A.H. Jin, S. Dutertre, D.J. Craik, Nucleic Acids Res. 40(2012) D325-330. doi: 10.1093/nar/gkr886
22. [22]
  J. Gehrmann, N.L. Daly, P.F. Alewood, D.J. Craik, J. Med. Chem. 42(1999) 2364-2372. doi: 10.1021/jm990114p
23. [23]
  B. Thomma, B. Cammue, K. Thevissen, Planta 216(2002) 193-202. doi: 10.1007/s00425-002-0902-6
24. [24]
  T. Ganz, Nat. Rev. Immunol. 3(2003) 710-720. doi: 10.1038/nri1180
25. [25]
  R.I. Lehrer, T. Ganz, Curr. Opin. Immunol. 14(2002) 96-102. doi: 10.1016/S0952-7915(01)00303-X
26. [26]
  D.J. Schibli, H.N. Hunter, V. Aseyev, et al., J. Biol. Chem. 277(2002) 8279-8289. doi: 10.1074/jbc.M108830200
27. [27]
  Y.Q. Tang, J. Yuan, G. Ösapay, et al., Science 286(1999) 498-502. doi: 10.1126/science.286.5439.498
28. [28]
  M.C. Alexander, T. Hong, L.M. Boo, et al., Proc. Natl. Acad. Sci. U. S. A. 99(2002) 1813-1818. doi: 10.1073/pnas.052706399
29. [29]
  M. Trabi, H.J. Schirra, D.J. Craik, Biochemistry 40(2001) 4211-4221. doi: 10.1021/bi002028t
30. [30]
  A.C. Conibear, K.J. Rosengren, N.L. Daly, S.T. Henriques, D.J. Craik, J. Biol. Chem. 288(2013) 10830-10840. doi: 10.1074/jbc.M113.451047
31. [31]
  D.J. Craik, N.L. Daly, T. Bond, C. Waine, J. Mol. Biol. 294(1999) 1327-1336. doi: 10.1006/jmbi.1999.3383
32. [32]
  S.T. Henriques, D.J. Craik, ACS Chem. Biol. 7(2012) 626-636. doi: 10.1021/cb200395f
33. [33]
  C.T.T. Wong, D.K. Rowlands, C.H. Wong, et al., Angew. Chem. Int. Ed. 51(2012) 5620-5624. doi: 10.1002/anie.201200984
34. [34]
  K. Jagadish, A. Gould, R. Borra, et al., Angew. Chem. Int. Ed. 54(2015) 8390-8394. doi: 10.1002/anie.201501186
35. [35]
  C.K. Wang, C.W. Gruber, M. Cemazar, et al., ACS Chem. Biol. 9(2014) 156-163. doi: 10.1021/cb400548s
36. [36]
  M.E. Felizmenio-Quimio, N.L. Daly, D.J. Craik, J. Biol. Chem. 276(2001) 22875-22882. doi: 10.1074/jbc.M101666200
37. [37]
  C. Jennings, J. West, C. Waine, D. Craik, M. Anderson, Proc. Natl. Acad. Sci. U. S. A. 98(2001) 10614-10619. doi: 10.1073/pnas.191366898
38. [38]
  M.L. Colgrave, A.C. Kotze, Y.H. Huang, et al., Biochemistry 47(2008) 5581-5589. doi: 10.1021/bi800223y
39. [39]
  M.R.R. Plan, I. Saska, A.G. Caguan, D.J. Craik, J. Agric. Food. Chem. 56(2008) 5237-5241. doi: 10.1021/jf800302f
40. [40]
  B. Chen, M.L. Colgrave, N.L. Daly, et al., J. Biol. Chem. 280(2005) 22395-22405. doi: 10.1074/jbc.M501737200
41. [41]
  S.T. Henriques, Y.H. Huang, S. Chaousis, et al., Chem. Biol. 22(2015) 1087-1097. doi: 10.1016/j.chembiol.2015.07.012
42. [42]
  H. Terlau, B.M. Olivera, Physiol. Rev. 84(2004) 41-68. doi: 10.1152/physrev.00020.2003
43. [43]
  W.R. Gray, B.M. Olivera, G.C. Zafaralla, et al., Biochemistry 31(1992) 11864-11873. doi: 10.1021/bi00162a027
44. [44]
  E. Leipold, A. Hansel, B.M. Olivera, H. Terlau, S.H. Heinemann, FEBS Lett. 579(2005) 3881-3884. doi: 10.1016/j.febslet.2005.05.077
45. [45]
  K.J. Shon, M. Stocker, H. Terlau, et al., J. Biol. Chem. 273(1998) 33-38. doi: 10.1074/jbc.273.1.33
46. [46]
  K.J. Nielsen, T. Schroeder, R. Lewis, J. Mol. Recognit. 13(2000) 55-70. doi: 10.1002/(ISSN)1099-1352
47. [47]
  R.A. Li, G.F. Tomaselli, Toxicon 44(2004) 117-122. doi: 10.1016/j.toxicon.2004.03.028
48. [48]
  G.P. Miljanich, Curr. Med. Chem. 11(2004) 3029-3040. doi: 10.2174/0929867043363884
49. [49]
  L. Moise, A. Piserchio, V.J. Basus, E. Hawrot, J. Biol. Chem. 277(2002) 12406-12417. doi: 10.1074/jbc.M110320200
50. [50]
  H.S. Young, L.G. Herbette, V. Skita, Biophys. J. 85(2003) 943-953. doi: 10.1016/S0006-3495(03)74533-0
51. [51]
  Y.H. Chen, J.C. Tai, W.J. Huang, et al., Biochemistry 21(1982) 2592-2600. doi: 10.1021/bi00540a003
52. [52]
  R. Doley, R.M. Kini, Cell. Mol. Life Sci. 66(2009) 2851-2871. doi: 10.1007/s00018-009-0050-2
53. [53]
  Y.C. Cheng, J.J. Wang, L.S. Chang, Toxicon 51(2008) 304-315. doi: 10.1016/j.toxicon.2007.10.006
54. [54]
  J.H. Shiu, C.Y. Chen, L.S. Chang, et al., Proteins 57(2004) 839-849. doi: 10.1002/(ISSN)1097-0134
55. [55]
  J.C. Dewan, G.A. Grant, J.C. Sacchettini, Biochemistry 33(1994) 13147-13154. doi: 10.1021/bi00248a026
56. [56]
  J. Ciolek, H. Reinfrank, L. Quinton, et al., Proc. Natl. Acad. Sci. U. S. A.114(2017) 7154-7159. doi: 10.1073/pnas.1620454114
57. [57]
  S. Diochot, A. Baron, M. Salinas, et al., Nature 490(2012) 552-555. doi: 10.1038/nature11494
58. [58]
  J.P. Rosso, J.R. Schwarz, M. Diaz-Bustamante, et al., Proc. Natl. Acad. Sci. U. S. A. 112(2015) E891-E900. doi: 10.1073/pnas.1415488112
59. [59]
  P. Hidalgo, R. Mackinnon, Science 268(1995) 307-310. doi: 10.1126/science.7716527
60. [60]
  R.C.R. Vega, L.D. Possani, Toxicon 43(2004) 865-875. doi: 10.1016/j.toxicon.2004.03.022
61. [61]
  T. Durek, I. Vetter, C.A. Wang, et al., ACS Chem. Biol. 8(2013) 1215-1222. doi: 10.1021/cb400012k
62. [62]
  J.J. Smith, J.M. Hill, M.J. Little, et al., Proc. Natl. Acad. Sci. U. S. A. 108(2011) 10478-10483. doi: 10.1073/pnas.1103501108
63. [63]
  M.L. Ruiz, R.L. Kraus, J. Med. Chem. 58(2015) 7093-7118. doi: 10.1021/jm501981g
64. [64]
  D.J. Craik, N.L. Daly, C. Waine, Toxicon 39(2001) 43-60. doi: 10.1016/S0041-0101(00)00160-4
65. [65]
  J.H. Park, K.P. Carlin, G. Wu, et al., J. Med. Chem. 57(2014) 6623-6631. doi: 10.1021/jm500687u
66. [66]
  J.D. Osteen, V. Herzig, J. Gilchrist, et al., Nature 534(2016) 494-499. doi: 10.1038/nature17976
67. [67]
  J. Siemens, S. Zhou, R. Piskorowski, et al., Nature 444(2006) 208-212. doi: 10.1038/nature05285
68. [68]
  C.J. Bohlen, A. Priel, S. Zhou, et al., Cell 141(2010) 834-845. doi: 10.1016/j.cell.2010.03.052
69. [69]
  M. Kita, D.S. Black, O. Ohno, et al., J. Am. Chem. Soc.131(2009) 18038-18039. doi: 10.1021/ja908148z
70. [70]
  S. Yang, Y. Xiao, D. Kang, et al., Proc. Natl. Acad. Sci. U. S. A.110(2013) 17534-17539. doi: 10.1073/pnas.1306285110
71. [71]
  Z.C. Liu, R. Zhang, F. Zhao, et al., J. Proteome Res. 11(2012) 6197-6212. doi: 10.1021/pr300881d
72. [72]
  P. Sun, F. Wu, M. Wen, et al., Sci. Rep. 5(2015) 13399. doi: 10.1038/srep13399
73. [73]
  M.J. Gallagher, K.M. Blumenthal, J. Biol. Chem. 269(1994) 254-259.
74. [74]
  Z. Dekan, S.J.Headey, M. Scanlon, et al., Angew. Chem. Int. Ed.56(2017) 8495-8499. doi: 10.1002/anie.201703360
75. [75]
  E. Habermann, Angew. Chem. Int. Ed. 12(1973) 83-84.
76. [76]
  A. Gould, Y. Li, S. Majumder, et al., Mol. BioSyst. 8(2012) 1359-1365. doi: 10.1039/c2mb05451e
77. [77]
  J.S. Zheng, S. Tang, G. Ye, H.N. Chang, L. Liu, ChemBioChem 13(2012) 542-546. doi: 10.1002/cbic.v13.4
78. [78]
  J.X. Wang, G.M. Fang, Y. He, et al., Angew. Chem. Int. Ed. 54(2015) 2194-2198. doi: 10.1002/anie.201408078
79. [79]
  M. Pan, Y. He, M. Wen, et al., Chem. Commun. 50(2014) 5837-5839. doi: 10.1039/C4CC00779D
80. [80]
  P.E. Dawson, T.W. Muir, I. Clark-Lewis, S.B.H. Kent, Science 266(1994) 776-779. doi: 10.1126/science.7973629
81. [81]
  G.M. Fang, J.X. Wang, L. Liu, Angew. Chem. Int. Ed. 51(2012) 10347-10350. doi: 10.1002/anie.201203843
82. [82]
  J.S. Zheng, S. Tang, Y.K. Qi, Z.P. Wang, L. Liu, Nat. Protoc. 8(2013) 2483-2495. doi: 10.1038/nprot.2013.152
83. [83]
  J.S. Zheng, H.N. Chang, F.L. Wang, L. Liu, J. Am. Chem. Soc. 133(2011) 11080-11083. doi: 10.1021/ja204088a
84. [84]
  S. Tang, Y.Y. Si, Z.P. Wang, et al., Angew. Chem. Int. Ed. 54(2015) 5713-5717. doi: 10.1002/anie.201500051
85. [85]
  G.M. Fang, Y.M. Li, F. Shen, et al., Angew. Chem. Int. Ed. 50(2011) 7645-7649. doi: 10.1002/anie.201100996
86. [86]
  Y.C. Huang, Y.M. Li, Y. Chen, et al., Angew. Chem. Int. Ed. 52(2013) 4858-4862. doi: 10.1002/anie.v52.18
87. [87]
  Y.M. Li, Y.T. Li, M. Pan, et al., Angew. Chem. Int. Ed. 53(2014) 2198-2202. doi: 10.1002/anie.201310010
88. [88]
  Z. Wang, W. Xu, L. Liu, T.F. Zhu, Nat. Chem. 8(2016) 698-704. doi: 10.1038/nchem.2517
89. [89]
  M. Pan, S. Gao, Y. Zheng, et al., J. Am. Chem. Soc. 138(2016) 7429-7435. doi: 10.1021/jacs.6b04031
90. [90]
  R. Zitterbart, O. Seitz, Angew. Chem. Int. Ed. 55(2016) 7252-7256. doi: 10.1002/anie.201601843
91. [91]
  S.F. Loibl, Z. Harpaz, O. Seitz, Angew. Chem. Int. Ed. 54(2015) 15055-15059. doi: 10.1002/anie.201505274
92. [92]
  M.M. Altamirano, C. García, L.D. Possani, A.R. Fersht, Nat. Biotechnol. 17(1999) 187-191. doi: 10.1038/6192
93. [93]
  M. Sela, F.H. White, C.B. Anfinsen, Science 125(1957) 691-692. doi: 10.1126/science.125.3250.691
94. [94]
  G. Bulaj, O. Buczek, I. Goodsell, et al., Proc. Natl. Acad. Sci. U. S. A. 100(2003) 14562-14568. doi: 10.1073/pnas.2335845100
95. [95]
  A. Schrimpf, U. Linne, A. Geyer, Org. Biomol. Chem. 15(2017) 2512-2521. doi: 10.1039/C6OB02746F
96. [96]
  V.P. Terrier, A.F. Delmas, V. Aucagne, Org. Biomol. Chem. 15(2017) 316-319. doi: 10.1039/C6OB02546C
97. [97]
  C.I. Schroeder, L.D. Rash, X. Vila-Farrés, et al., Angew. Chem. Int. Ed. 53(2014) 1017-1020. doi: 10.1002/anie.201308898
98. [98]
  B. Dang, T. Kubota, A.M. Correa, F. Bezanilla, S.B.H. Kent, Angew. Chem. Int. Ed. 53(2014) 8970-8974. doi: 10.1002/anie.201404438
99. [99]
  B. Dang, T. Kubota, K. Mandal, et al., Angew. Chem. Int. Ed. 55(2016) 8639-8642. doi: 10.1002/anie.201603420
100. [100]
  B. Dang, T. Kubota, K. Mandal, F. Bezanilla, S.B.H. Kent, J. Am. Chem. Soc. 135(2013) 11911-11919. doi: 10.1021/ja4046795
101. [101]
  M. Góngora-Benítez, J. Tulla-Puche, F. Albericio, Chem. Rev. 114(2014) 901-926. doi: 10.1021/cr400031z
102. [102]
  T.M. Postma, F. Albericio, Eur. J. Org. Chem. 17(2014) 3519-3530.
103. [103]
  H. Hibino, Y. Miki, Y. Nishiuchi, J. Pept. Sci. 20(2014) 30-35. doi: 10.1002/psc.v20.1
104. [104]
  Y.K. Qi, S. Tang, Y.C. Huang, et al., Org. Biomol. Chem. 14(2016) 4194-4198. doi: 10.1039/C6OB00450D
105. [105]
  B.L. Pentelute, S.B.H. Kent, Org. Lett. 9(2007) 687-690. doi: 10.1021/ol0630144
106. [106]
  X. Yang, V. Gelfanov, F. Liu, R. DiMarchi, Org. Lett. 18(2016) 5516-5519. doi: 10.1021/acs.orglett.6b02751
107. [107]
  S.K. Maity, M. Jbara, S. Laps, A. Brik, Angew. Chem. Int. Ed. 55(2016) 8108-8112. doi: 10.1002/anie.201603169
108. [108]
  M. Jbara, S.K. Maity, A. Brik, Angew. Chem. Int. Ed. 56(2017) 10644-10655. doi: 10.1002/anie.201702370
109. [109]
  T.D. Kondasinghe, H.Y. Saraha, S.B. Odeesho, J.L. Stockdill, Org. Biomol. Chem. 15(2017) 2914-2918. doi: 10.1039/C7OB00536A
110. [110]
  T.M. Postma, M. Giraud, F. Albericio, Org. Lett. 14(2012) 5468-5471. doi: 10.1021/ol3025499
111. [111]
  M. Muttenthaler, Y.G. Ramos, D. Feytens, A.D. de Araujo, P.F. Alewood, Pept. Sci. 94(2010) 423-432. doi: 10.1002/bip.21502
112. [112]
  A. Brust, C.I.A. Wang, N.L. Daly, et al., Angew. Chem. Int. Ed. 52(2013) 12020-12023. doi: 10.1002/anie.201304660
113. [113]
  F. Shen, Z.P. Zhang, J.B. Li, Y. Lin, L. Liu, Org. Lett. 13(2011) 568-571. doi: 10.1021/ol1028755
114. [114]
  Z. Dekan, M. Mobli, M.W. Pennington, et al., Angew. Chem. Int. Ed. 53(2014) 2931-2934. doi: 10.1002/anie.v53.11
115. [115]
  J.L. Stymiest, B.F. Mitchell, S. Wong, J.C. Vederas, Org. Lett. 5(2003) 47-49. doi: 10.1021/ol027160v
116. [116]
  D.J. Derksen, J.L. Stymiest, J.C. Vederas, J. Am. Chem. Soc. 128(2006) 14252-14253. doi: 10.1021/ja066203q
117. [117]
  S. Chhabra, A. Belgi, P. Bartels, et al., J. Med. Chem. 57(2014) 9933-9944. doi: 10.1021/jm501126u
118. [118]
  B.J. van Lierop, S.D. Robinson, S.N. Kompella, et al., ACS Chem. Biol. 8(2013) 1815-1821. doi: 10.1021/cb4002393
119. [119]
  A. Glas, D. Bier, G. Hahne, et al., Angew. Chem. Int. Ed. 53(2014) 2489-2493. doi: 10.1002/anie.201310082
120. [120]
  A. Glas, T.N. Grossmann, Synletter 26(2015) 1-5. doi: 10.1055/s-00000083
121. [121]
  H.K. Cui, Y. Guo, Y. He, et al., Angew. Chem. Int. Ed. 52(2013) 9558-9562. doi: 10.1002/anie.v52.36
122. [122]
  Y. Guo, D.M. Sun, F.L. Wang, et al., Angew. Chem. Int. Ed. 54(2015) 14276-14281. doi: 10.1002/anie.201500699
123. [123]
  Y. Xu, T. Wang, C.J. Guan, et al., Tetrahedron Lett. 58(2017) 1677-1680. doi: 10.1016/j.tetlet.2017.03.024
124. [124]
  Y. Guo, C. Liu, H. Song, et al., RSC Adv. 7(2017) 2110-2114. doi: 10.1039/C6RA26617G
125. [125]
  Y. Wu, Y.H. Li, X. Li, et al., Chem. Sci. 8(2017) 7368-7373. doi: 10.1039/C7SC02420G
126. [126]
  Y. Xu, L. Xu, Y. Xia, et al., Chem. Commun. 51(2015) 13189-13192.
127. [127]
  P.J. Knerr, W.A. van der Donk, Ann. Rev. Biochem. 81(2012) 479-505. doi: 10.1146/annurev-biochem-060110-113521
128. [128]
  L. Huo, W.A. van der Donk, J. Am. Chem. Soc. 138(2016) 5254-5257. doi: 10.1021/jacs.6b02513
129. [129]
  J.P. Mayer, J.R. Heil, J. Zhang, M.C. Munson, Tetrahedron Lett. 36(1995) 7387-7390. doi: 10.1016/0040-4039(95)01548-5
130. [130]
  Y. Wang, D.H. Chou, Angew. Chem. Int. Ed. 54(2015) 10931-10934. doi: 10.1002/anie.201503975
131. [131]
  K. Hu, H. Geng, Q. Zhang, et al., Angew. Chem. Int. Ed. 55(2016) 8013-8017. doi: 10.1002/anie.201602806
132. [132]
  P.J. Knerr, A. Tzekou, D. Ricklin, et al., ACS Chem. Biol. 6(2011) 753-760. doi: 10.1021/cb2000378
133. [133]
  B. Zhao, D. Yang, J.H. Wong, et al., ChemBioChem 17(2016) 1416-1420. doi: 10.1002/cbic.v17.15
134. [134]
  Z.V.F. Wright, S. McCarthy, R. Dickman, et al., J. Am. Chem. Soc. 139(2017) 13063-13075. doi: 10.1021/jacs.7b06506
135. [135]
  C.M.B.K. Kourra, N. Cramer, Chem. Sci. 7(2016) 7007-7012. doi: 10.1039/C6SC02285E
136. [136]
  H.J. Reich, R.J. Hondal, ACS Chem. Biol. 11(2016) 821-841. doi: 10.1021/acschembio.6b00031
137. [137]
  A.D. de Araujo, M. Mobli, J. Castro, et al., Nat. Commun. 5(2014) 3165. doi: 10.1038/ncomms4165
138. [138]
  A.D. de Araujo, M. Mobli, G.F. King, P.F. Alewood, Angew. Chem. Int. Ed. 51(2012) 10298-10302. doi: 10.1002/anie.201204229
139. [139]
  A.D. de Araujo, B. Callaghan, S.T. Nevin, et al., Angew. Chem. Int. Ed. 50(2011) 6527-6529. doi: 10.1002/anie.v50.29
140. [140]
  M. Mobli, A.D. de Araújo, L.K. Lambert, et al., Angew. Chem. Int. Ed. 48(2009) 9312-9314. doi: 10.1002/anie.v48:49
141. [141]
  M. Muttenthaler, S.T. Nevin, A.A. Grishin, et al., J. Am. Chem. Soc. 132(2010) 3514-3522. doi: 10.1021/ja910602h
142. [142]
  N.E. Shepherd, H.N. Hoang, G. Abbenante, D.P. Fairlie, J. Am. Chem. Soc. 127(2005) 2974-2983. doi: 10.1021/ja0456003
143. [143]
  H.N. Hoang, R.W. Driver, R.L. Beyer, et al., Angew. Chem. Int. Ed. 55(2016) 8275-8279. doi: 10.1002/anie.201602079
144. [144]
  H. Zhao, Q.S. Liu, H. Geng, et al., Angew. Chem. Int. Ed. 55(2016) 12088-12093. doi: 10.1002/anie.201606833
145. [145]
  Y. Tian, X. Zeng, J. Li, et al., Chem. Sci. 8(2017) 7576-7581. doi: 10.1039/C7SC03614K
146. [146]
  H. Zhao, Y. Jiang, Y. Tian, et al., Org. Biomol. Chem. 15(2017) 459-464. doi: 10.1039/C6OB02501C
147. [147]
  B. Hargittai, N.A. Solé, D.R. Groebe, S.N. Abramson, G. Barany, J. Med. Chem. 43(2000) 4787-4792. doi: 10.1021/jm990635c
148. [148]
  K.K. Khoo, M.J. Wilson, B.J. Smith, et al., J. Med. Chem. 54(2011) 7558-7566. doi: 10.1021/jm200839a
149. [149]
  C.W. Tornfe, C. Christensen, M. Meldal, J. Org. Chem. 67(2002) 3057-3064. doi: 10.1021/jo011148j
150. [150]
  V.V. Rostovtsev, G.L. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41(2002) 2596-2599. doi: 10.1002/(ISSN)1521-3773
151. [151]
  M. Fmpting, O. Avrutina, R. Meusinger, et al., Angew. Chem. Int. Ed. 50(2011) 5207-5211. doi: 10.1002/anie.v50.22
152. [152]
  S. Pacifico, A. Kerckhoffs, A.J.Fallow, et al., Org. Biomol. Chem.15(2017) 4704-4710. doi: 10.1039/C7OB00959C
153. [153]
  K. Holland-Nell, M. Meldal, Angew. Chem. Int. Ed. 50(2011) 5204-5206. doi: 10.1002/anie.v50.22
154. [154]
  A. Gori, C.I.A. Wang, P.J. Harvey, et al., Angew. Chem. Int. Ed. 54(2015) 1361-1364. doi: 10.1002/anie.201409678
155. [155]
  M. Empting, O. Avrutina, R. Meusinger, et al., Angew. Chem. Int. Ed. 50(2011) 5207-5211. doi: 10.1002/anie.v50.22
156. [156]
  A.M. Spokoyny, Y. Zou, J.J. Ling, et al., J. Am. Chem. Soc.135(2013) 5946-5949. doi: 10.1021/ja400119t
157. [157]
  Y. Zheng, L. Zhai, Y. Zhao, C. Wu, J. Am. Chem. Soc. 137(2015) 15094-15097. doi: 10.1021/jacs.5b10779
158. [158]
  W. Liu, Y. Zheng, X. Kong, et al., Angew. Chem. Int. Ed. 56(2017) 4458-4463. doi: 10.1002/anie.201610942
159. [159]
  Y. Chen, T. Li, J. Li, et al., Org. Biomol. Chem. 15(2017) 1921-1929. doi: 10.1039/C6OB02786E
160. [160]
  T. Lühmann, S.K. Mong, M.D. Simon, L. Meinel, B.L. Pentelute, Org. Biomol. Chem. 14(2016) 3345-3349. doi: 10.1039/C6OB00208K
161. [161]
  S. Rapireddy, L. Nhon, R.E. Meehan, et al., J. Am. Chem. Soc.134(2012) 4041-4044. doi: 10.1021/ja211867j
162. [162]
  J.A. Getz, O. Cheneval, D.J. Craik, P.S. Daugherty, ACS Chem. Biol. 8(2013) 1147-1154. doi: 10.1021/cb4000585
163. [163]
  Y.P. Chang, J. Banerjee, C. Dowell, et al., J. Med. Chem. 57(2014) 3511-3521. doi: 10.1021/jm500183r
164. [164]
  R. Zhao, H. Dai, N. Mendelman, et al., Proc. Natl. Acad. Sci. U. S. A. 112(2015) E7013-7021. doi: 10.1073/pnas.1514728112
165. [165]
  J.S. Zheng, S. Tang, Y.C. Huang, L. Liu, Acc. Chem. Res. 46(2013) 2475-2484. doi: 10.1021/ar400012w
166. [166]
  Y.C. Huang, G.M. Fang, L. Liu, Natl. Sci. Rev. 3(2016) 107-116. doi: 10.1093/nsr/nwv072
167. [167]
  J.B. Li, S. Tang, J.S. Zheng, C.L. Tian, L. Liu, Acc. Chem. Res. 50(2017) 1143-1153. doi: 10.1021/acs.accounts.7b00001
168. [168]
  B. Yan, L. Ye, W. Xu, L. Liu, Bioorg. Med. Chem. 25(2017) 4953-4965. doi: 10.1016/j.bmc.2017.05.020
169. [169]
  B. Farrow, M. Wong, J. Malette, et al., Angew. Chem. Int. Ed. 54(2015) 7114-7119. doi: 10.1002/anie.201502451
170. [170]
  Z. Zhu, A. Shaginian, L.S.C. Grady, et al., ACS Chem. Biol. 13(2018) 53-59. doi: 10.1021/acschembio.7b00852
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