Citation: Luo Huiyun, Yin Hongli, Tang Chaojun, Wang Ping, Liang Feng. Synthesis of cyclic peptide reniochalistatin E and conformational isomers[J]. Chinese Chemical Letters, ;2018, 29(7): 1143-1146. doi: 10.1016/j.cclet.2018.05.033 shu

Synthesis of cyclic peptide reniochalistatin E and conformational isomers

Luo Huiyun ^a ,
Yin Hongli ^b ,
Tang Chaojun ^c ,
Wang Ping ^b,, ,
Liang Feng ^a,,

a.
The State Key Laboratory of Refractories and Metallurgy, School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, China
b.
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China
c.
Chonqqing Huapont Pharm. Co., Ltd., Chongqing 401121, China

Corresponding author: Wang Ping, wangp1@sjtu.edu.cn Liang Feng, feng_liang@wust.edu.cn
Received Date: 15 March 2018
Revised Date: 17 May 2018
Accepted Date: 18 May 2018
Available Online: 18 July 2018

Figures(4)

Here, we report a convenient and efficient synthesis strategy for the total synthesis of cyclic peptide reniochalistatin E and its conformational isomers with 32% overall yield. We found the linear peptide precursor without side chain gave better cyclization yield.
- Cyclic peptide,
- Reniochalistatin E,
- Solid-phase peptide synthgesis,
- Conformational isomers
1. [1]
  T. Doi, S. Kamioka, S. Shimazu, T. Takahashi, Org. Lett. 10(2008) 817-819. doi: 10.1021/ol702965r
2. [2]
  H.M. Geng, Q.Y. Zong, J. You, et al., Sci. China Chem. 59(2016) 293-302. doi: 10.1007/s11426-015-5477-8
3. [3]
  K. Burgess, D. Lim, C.I. Martinez, Angew. Chem. Int. Ed. 35(1996) 1077-1078.
4. [4]
  C. Thompson, M. Ge, D. Kahne, J. Am. Chem. Soc. 121(1999) 1237-1244. doi: 10.1021/ja983504u
5. [5]
  M.B. Choussy, L. Neuville, R. Beugelmans, J.P. Zhu, J. Org. Chem. 61(1996) 9309-9322. doi: 10.1021/jo961412m
6. [6]
  X.Y. Wu, J.L. Stockdill, P. Wang, S.J. Danishefsky, J. Am. Chem. Soc. 132(2012) 4098-4100.
7. [7]
  H.Y. Lam, Y.F. Zhang, H. Liu, et al., J. Am. Chem. Soc. 135(2013) 6272-6279. doi: 10.1021/ja4012468
8. [8]
  K. Jin, I.H. Sam, K.H.L. Po, et al., Nat. Commun. 7(2016) 12394-12399. doi: 10.1038/ncomms12394
9. [9]
  A.M. Giltrap, L.J. Dowman, G. Nagalingam, et al., Org. Lett.18(2016) 2788-2791. doi: 10.1021/acs.orglett.6b01324
10. [10]
  P. Desai, S.S. Pfeiffer, D.L. Boger, Org. Lett. 5(2003) 5047-5050. doi: 10.1021/ol036083g
11. [11]
  K.X. Zhan, W.H. Jiao, F. Yang, et al., J. Nat. Prod. 77(2014) 2678-2684. doi: 10.1021/np5006778
12. [12]
  A. Fatino, G. Baca, C. Weeramange, et al., J. Nat. Prod. 80(2017) 3234-3240. doi: 10.1021/acs.jnatprod.7b00656
13. [13]
  R.B. Merrifield, J. Am. Chem. Soc. 85(1963) 2149-2154. doi: 10.1021/ja00897a025
14. [14]
  H.K. Cui, Y. Guo, Y. He, et al., Angew. Chem. Int. Ed. 52(2013) 9558-9562. doi: 10.1002/anie.v52.36
15. [15]
  C.M. Zhang, J.X. Guo, L. Wang, et al., Chin. Chem. Lett. 22(2011) 631-634. doi: 10.1016/j.cclet.2010.12.039
16. [16]
  J. Chen, B. Zhang, C. Xie, Y. Lu, W. Wu, Chin. Chem. Lett. 21(2010) 391-394. doi: 10.1016/j.cclet.2009.11.026
17. [17]
  P.J. Knerr, W.A. Donk, J. Am. Chem. Soc. 135(2013) 7094-7097. doi: 10.1021/ja4014024
18. [18]
  H. Zheng, F. Wang, Q. Wang, J.M. Gao, J. Am. Chem. Soc. 133(2011) 15280-15283. doi: 10.1021/ja205911n
19. [19]
  Z.M. Wu, S.Z. Liu, X.Z. Cheng, X.R. Zhao, H.F. Hong, Chin. Chem. Lett. 28(2017) 553-557. doi: 10.1016/j.cclet.2016.11.001
20. [20]
  E.K. Singh, D.M. Ramsey, S.R. McAlpine, Org. Lett. 14(2012) 1198-1201. doi: 10.1021/ol203290n
21. [21]
  K. Barlos, D. Gatos, J. Kallitsis, et al., Tetrahedron Lett. 30(1989) 3943-3946. doi: 10.1016/S0040-4039(00)99290-6
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