Citation: Tan Xiaodan, Bai Jingsi, Ding Shan, Ren Yujing, Hong Danning, Mei Ziqing, Li Yi-Ming. Semi-synthesis of Ubiquitin-propargylamide for identifying deubiquitinase targeting inhibitors[J]. Chinese Chemical Letters, ;2019, 30(3): 743-746. doi: 10.1016/j.cclet.2018.09.003 shu

Semi-synthesis of Ubiquitin-propargylamide for identifying deubiquitinase targeting inhibitors

Tan Xiaodan ^a,b,1 ,
Bai Jingsi ^a,1 ,
Ding Shan ^c ,
Ren Yujing ^d,c ,
Hong Danning ^d,c ,
Mei Ziqing ^c,*, ,
Li Yi-Ming ^a,*,

a.
School of Biological and Medical Engineering, Hefei University of Technology, Hefei 230009, China
b.
Tsinghua-Peking Center for Life Sciences, Ministry of Education Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing 100084, China
c.
Biotechnology Research Institute, Chinese Academy of Agricultural Sciences, Beijing 100081 China
d.
School of Biological Science, Beijing Institute of Technology, Beijing 100084, China

meiziqing@caas.cn

ymli@hfut.edu.cn

Received Date: 18 July 2018
Revised Date: 4 September 2018
Accepted Date: 6 September 2019
Available Online: 7 March 2018

Figures(5)

Ubiquitin-propargylamide (Ub-PA) is one of the most widely used activity-based probe to measure the activity of deubiquitinases (DUBs) and help validate DUBs targeting inhibitors. However, current synthetic route of Ub-PA is cumbersome. In this work, we report a novel semi-synthetic strategy to prepare Ub-PA in large-scale. Biochemical assays prove that semi-synthetic Ub-PA is an effective probe in identifying DUBs targeting inhibitors.
- Deubiquitinase,
- Activity-based probe,
- Ubiquitin-propargylamide,
- Protein semi-synthesis,
- Inhibitor identification
1. [1]
  D. Komander, M. Rape, Annu. Rev. Biochem. 81(2012) 203-229. doi: 10.1146/annurev-biochem-060310-170328
2. [2]
  A. Ciechanover, Nat. Rev. Mol. Cell Biol. 16(2015) 322-324. doi: 10.1038/nrm3982
3. [3]
  D. Komander, M.J. Clague, S. Urbé, Nat. Rev. Mol. Cell Biol. 10(2009) 550-563. doi: 10.1038/nrm2731
4. [4]
  T.E. Mevissen, D. Komander, Annu. Rev. Biochem. 86(2017) 159-192. doi: 10.1146/annurev-biochem-061516-044916
5. [5]
  J.A. Harrigan, X. Jacq, N.M. Martin, et al., Nat. Rev. Drug Discov.17(2018) 57-77.
6. [6]
  H. Jung, B.G. Kim, W.H. Han, et al., Oncogenesis 2(2013) e64. doi: 10.1038/oncsis.2013.28
7. [7]
  P. D'arcy, S. Brnjic, M.H. Olofsson, et al., Nat. Med. 17(2011) 1636-1640. doi: 10.1038/nm.2536
8. [8]
  M.I. Davis, A. Simeonov, Drug Target Rev. 2(2015) 60-64.
9. [9]
  X. Huang, V.M. Dixit, Cell Res. 26(2016) 484-498. doi: 10.1038/cr.2016.31
10. [10]
  Y. Leestemaker, H. Ovaa, Drug Discov. Today Technol. 26(2017) 25-31. doi: 10.1016/j.ddtec.2017.11.006
11. [11]
  D.S. Hewings, J.A. Flygare, M. Bogyo, et al., FEBS J. 284(2017) 1555-1576. doi: 10.1111/febs.14039
12. [12]
  G.B. Tilburg, A.F. Elhebieshy, H. Ovaa, Opin. Struct. Biol. 38(2016) 92-101. doi: 10.1016/j.sbi.2016.05.022
13. [13]
  Y. Liu, H.A. Lashuel, S. Choi, et al., Chem. Biol. 10(2003) 837-846. doi: 10.1016/j.chembiol.2003.08.010
14. [14]
  A.P. Turnbull, S. Ioannidis, W.W. Krajewski, Nature 550(2017) 481-486. doi: 10.1038/nature24451
15. [15]
  Y.T. Li, Y.C. Huang, Y. Xu, et al., Tetrahedron 72(2016) 4085-4090. doi: 10.1016/j.tet.2016.05.041
16. [16]
  G.C. Chu, J.S. Bai, Y.F. Kong, et al., Tetrahedron 74(2018) 3931-3935. doi: 10.1016/j.tet.2018.05.081
17. [17]
  C. Reverdy, S. Conrath, R. Lopez, et al., Chem. Biol. 19(2012) 467-477. doi: 10.1016/j.chembiol.2012.02.007
18. [18]
  A.H. Mermerian, A. Case, R.L. Stein, et al., Bioorg. Med. Chem. Lett. 17(2007) 3729-3732. doi: 10.1016/j.bmcl.2007.04.027
19. [19]
  B.H. Lee, M.J. Lee, S. Park, et al., Nature 467(2010) 179-181. doi: 10.1038/nature09299
20. [20]
  C. Ndubaku, V. Tsui, J. Med. Chem. 58(2014) 1581-1595.
21. [21]
  B. Nicholson, S. Kumar, S. Agarwal, et al., J. Biomol. Screen. 19(2014) 989-999. doi: 10.1177/1087057114527312
22. [22]
  R. Ekkebus, S.I. van Kasteren, Y. Kulathu, et al., J. Am. Chem. Soc. 135(2013) 2867-2870. doi: 10.1021/ja309802n
23. [23]
  A.P. Lawson, D.W. Bak, D.A. Shannon, et al., Oncotarget 8(2017) 51296.
24. [24]
  T.E. Mevissen, M.K. Hospenthal, P.P. Geurink, et al., Cell 154(2013) 69-184.
25. [25]
  F. El Oualid, R. Merkx, R. Ekkebus, et al., Angew. Chem. Int. Ed. 49(2010) 10149-10153. doi: 10.1002/anie.201005995
26. [26]
  A.L. Adams, B. Cowper, R.E. Morgan, et al., Angew. Chem. Int. Ed. 125(2013) 13300-13304. doi: 10.1002/ange.201304997
27. [27]
  L. Xu, J.F. Huang, C.C. Chen, et al., Org. Lett. 20(2017) 329-332.
28. [28]
  G.M. Fang, Y.M. Li, F. Shen, et al., Angew. Chem. Int. Ed. 50(2011) 7645-7649. doi: 10.1002/anie.201100996
29. [29]
  T. Curtius, J. Prakt. Chem. 70(1904) 57-72. doi: 10.1002/prac.19040700103
30. [30]
  N. Fujii, H. Yajima, J. Chem. Soc. Perkin Trans. 1(1981) 831-841.
31. [31]
  J.S. Zheng, S. Tang, Y.K. Qi, et al., Nat. Protoc. 8(2013) 2483-2495. doi: 10.1038/nprot.2013.152
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