Citation: Zhu Tong, Song Lu, Li Ruifeng, Wu Bian. Enzymatic clickable functionalization of peptides via computationally engineered peptide amidase[J]. Chinese Chemical Letters, ;2018, 29(7): 1116-1118. doi: 10.1016/j.cclet.2018.03.033 shu

Enzymatic clickable functionalization of peptides via computationally engineered peptide amidase

Zhu Tong ^a,b,1 ,
Song Lu ^a,c,1 ,
Li Ruifeng ^a,b ,
Wu Bian ^a,,

a.
CAS Key Laboratory of Microbial Physiological and Metabolic Engineering, State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China
b.
University of Chinese Academy of Sciences, Beijing 100101, China
c.
State Key Laboratory of Transducer Technology, Chinese Academy of Sciences, Beijing 100101, China

Corresponding author: Wu Bian, wub@im.ac.cn

Received Date: 5 February 2018
Revised Date: 21 March 2018
Accepted Date: 23 March 2018
Available Online: 30 July 2018

Figures(2)

Directed peptides C-terminal modification enabled by the engineered biomolecular catalyst-peptide amidase 12B has been achieved via computational protein engineering. The engineered enzyme exhibits great promising potential in the C-terminal modification of opioid peptides using prop-2-yn-1-amine (PYA) or prop-2-en-1-amine (PEA) as the nucleophile. A variety of opioid peptides could be readily functionalized at the C-terminal chain in high yield in a mild and selective manner. Notably, modified opioid peptides bearing alkynyl moiety could be further functionalized through well-established click reaction.
- Peptide amidase,
- Opioid peptides,
- C-terminal modification,
- Click reaction,
- Functionalization
1. [1]
  A. Kaspar, J.M. Reichert, Drug Discov. Today 18(2013) 807-817. doi: 10.1016/j.drudis.2013.05.011
2. [2]
  W.X. Liu, R. Wang, Med. Res. Rev. 32(2012) 536-580. doi: 10.1002/med.2012.32.issue-3
3. [3]
  E.M. Sletten, C.R. Bertozzi, Angew. Chem. Int. Ed. 48(2009) 6974-6998. doi: 10.1002/anie.v48:38
4. [4]
  H. Noda, G. ErÅs, J.W. Bode, J. Am. Chem. Soc. 136(2014) 5611-5614. doi: 10.1021/ja5018442
5. [5]
  M.E.B. Smith, F.F. Schumacher, C.P. Ryan, et al., J. Am. Chem. Soc. 132(2010) 1960-1965. doi: 10.1021/ja908610s
6. [6]
  A. Dondoni, Angew. Chem. Int. Ed. 47(2008) 8995-8997. doi: 10.1002/anie.v47:47
7. [7]
  Y.M. Li, Y.T. Li, M. Pan, et al., Angew. Chem. Int. Ed. 53(2014) 2198-2202. doi: 10.1002/anie.201310010
8. [8]
  O. Boutureira, G.J.L. Bernardes, Chem. Rev. 115(2015) 2174-2195. doi: 10.1021/cr500399p
9. [9]
  L. Schmohl, D. Schwarzer, Curr. Opin. Chem. Biol. 22(2014) 122-128. doi: 10.1016/j.cbpa.2014.09.020
10. [10]
  Z. Wu, X. Guo, Z. Guo, Chem. Commun. 46(2010) 5773-5774. doi: 10.1039/c0cc00828a
11. [11]
  T. Sijbrandij, N. Cukkemane, K. Nazmi, E.C.I. Veerman, F.J. Bikker, Bioconjugate Chem. 24(2013) 828-831. doi: 10.1021/bc4000146
12. [12]
  X.L. Tan, M. Pan, Y. Zheng, et al., Chem. Sci. 8(2017) 6881-6887. doi: 10.1039/C7SC02937C
13. [13]
  M.P. Davis, Expert Opin. Drug Discov. 5(2010) 1007-1022. doi: 10.1517/17460441.2010.511473
14. [14]
  B.L. Kieffer, Trends Pharmacol. Sci. 20(1999) 19-26. doi: 10.1016/S0165-6147(98)01279-6
15. [15]
  Z.H. Gu, B. Wang, Z.Z. Kou, et al., Neurosignals 25(2017) 98-116. doi: 10.1159/000484909
16. [16]
  S. Martin-Schild, J.E. Zadina, A.A. Gerall, S. Vigh, A.J. Kastin, Peptides 18(1997) 1641-1649. doi: 10.1016/S0196-9781(97)00320-3
17. [17]
  C. Tömböly, A. Péter, G. Tóth, Peptides 23(2002) 1573-1580. doi: 10.1016/S0196-9781(02)00100-6
18. [18]
  A. Janecka, R. Perlikowska, K. Gach, A. Wyrebska, J. Fichna, Curr. Pharm. Design 16(2010) 1126-1135. doi: 10.2174/138161210790963869
19. [19]
  C.P. Guimaraes, M.D. Witte, C.S. Theile, et al., Nat. Protoc. 8(2013) 1787-1799. doi: 10.1038/nprot.2013.101
20. [20]
  A. El Dahshan, S. Weik, J. Rademann, Org. Lett. 9(2007) 949-952. doi: 10.1021/ol062754+
21. [21]
  R. Schwyzer, Biochemistry 25(1986) 6335-6342. doi: 10.1021/bi00368a075
22. [22]
  P. Cherkupally, G.A. Acosta, S. Ramesh, et al., Amino Acids 46(2014) 1827-1838. doi: 10.1007/s00726-014-1746-7
23. [23]
  J.A. Fehrentz, M. Paris, A. Heitz, et al., J. Org. Chem. 62(1997) 6792-6796. doi: 10.1021/jo962408d
24. [24]
  L. Ju, J.W. Bode, Org. Biomol. Chem. 7(2009) 2259-2264. doi: 10.1039/b901198f
25. [25]
  A. Lindqvist, S. Jönsson, M. Hammarlund-Udenaes, Mol. Pharm. 13(2016) 1258-1266. doi: 10.1021/acs.molpharmaceut.5b00835
26. [26]
  Y. Koda, M.D. Borgo, S.T. Wessling, et al., Bioorg. Med. Chem. 16(2008) 6286-6296. doi: 10.1016/j.bmc.2008.04.020
27. [27]
  G. Zhang, S. Zheng, H. Liu, P.R. Chen, Chem. Soc. Rev. 44(2015) 3405-3417. doi: 10.1039/C4CS00393D
28. [28]
  B. Wu, H.J. Wijma, L. Song, et al., ACS Catal. 6(2016) 5405-5414. doi: 10.1021/acscatal.6b01062
29. [29]
  J. Hughes, T.W. Smith, H.W. Kosterlitz, et al., Nature 258(1975) 577-579. doi: 10.1038/258577a0
30. [30]
  S. Udenfriend, D.L. Kilpatrick, Arch. Biochem. Biophys. 221(1983) 309-323. doi: 10.1016/0003-9861(83)90149-2
31. [31]
  Y. Li, M.R. Lefever, D. Muthu, et al., Future Med. Chem. 4(2012) 205-226. doi: 10.4155/fmc.11.195
32. [32]
  M.S. Henry, L. Gendron, M.E. Tremblay, G. Drolet, Neural. Plast (2017) Article ID 1546125.
33. [33]
  D. Owczarek, D. Cibor, T. Mach, et al., Adv. Med. Sci. 56(2011) 158-164. doi: 10.2478/v10039-011-0051-x
34. [34]
  J.E. Zadina, L. Hackler, L.J. Ge, A.J. Kastin, Nature 386(1997) 499-502. doi: 10.1038/386499a0
35. [35]
  S. Martin-Schild, A.A. Gerall, A.J. Kastin, J.E. Zadina, Peptides 19(1998) 1783-1789. doi: 10.1016/S0196-9781(98)00136-3
36. [36]
  D.D. Nguyen, S.K. Johnson, F. Busetti, V.A. Solah, Crit. Rev. Food Sci. Nutr. 55(2015) 1955-1967. doi: 10.1080/10408398.2012.740102
37. [37]
  H. Teschemacher, G. Koch, V. Brantl, Biopolymers 43(1997) 99-117.
38. [38]
  C.M. Dundas, D. Demonte, S. Park, Appl. Microbiol. Biotechnol. 97(2013) 9343-9353. doi: 10.1007/s00253-013-5232-z
39. [39]
  S. Li, L. Wang, F. Yu, et al., Chem. Sci. 8(2017) 2107-2114. doi: 10.1039/C6SC02297A
40. [40]
  L. Li, Z. Zhang, Molecules 21(2016) 1393-1415. doi: 10.3390/molecules21101393
41. [41]
  B.L. Oliveira, Z. Guo, G.J.L. Bernardes, Chem. Soc. Rev. 46(2017) 4895-4950. doi: 10.1039/C7CS00184C
42. [42]
  A. Borrmann, S. Milles, T. Plass, et al., Chembiochem 13(2012) 2094-2099. doi: 10.1002/cbic.v13.14
43. [43]
  T. Smyth, K. Petrova, N.M. Payton, et al., Bioconjugate Chem. 25(2014) 1777-1784. doi: 10.1021/bc500291r
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  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
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  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
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