Theoretical investigations on the thiol-thioester exchange steps of different thioesters

注册 English

Theoretical investigations on the thiol-thioester exchange steps of different thioesters

Xiao-Hui Sun , Hai-Zhu Yu , Shu-Qi Pei , Zhi-Min Dang

Citation: Xiao-Hui Sun, Hai-Zhu Yu, Shu-Qi Pei, Zhi-Min Dang. Theoretical investigations on the thiol-thioester exchange steps of different thioesters[J]. Chinese Chemical Letters, 2015, 26(10): 1259-1264. doi: 10.1016/j.cclet.2015.07.003 shu

shu

Theoretical investigations on the thiol-thioester exchange steps of different thioesters

通讯作者: Hai-Zhu Yu,
Zhi-Min Dang,

基金项目:
We appreciate NSFC (No. 21202006) (No. 21202006)

FRFCU (No. FRF-TP- 14-015A2) for financial supports (No. FRF-TP- 14-015A2)

摘要: As the rate-determining step in native chemical ligation reactions, the thiol-thioester exchange step is important in determining the efficiency of the ligations of peptides. In the present study, systematic theoretical calculations were carried out on the relationships between the structure of different thioesters and the free energy barriers of the thiol-thioester exchange step. According to the calculation results, the thiol-thioester exchange step is disfavored by the steric hindrance around the carbonyl center, while the electronic effect (i.e. conjugation and hyper-conjugation effects) becomes important when the steric hindrance is insignificant.

关键词:

English

Theoretical investigations on the thiol-thioester exchange steps of different thioesters

1.
1 Department of Polymer Science and Engineering, University of Science and Technology Beijing, Beijing 100083, China;
2.
2 Department of Chemistry and Centre for Atomic Engineering of Advanced Materials, Anhui University, Hefei 230601, China

Corresponding author: Hai-Zhu Yu, Zhi-Min Dang,

Received Date: 09 April 2015
Available Online: 06 July 2015
Fund Project:

Abstract: As the rate-determining step in native chemical ligation reactions, the thiol-thioester exchange step is important in determining the efficiency of the ligations of peptides. In the present study, systematic theoretical calculations were carried out on the relationships between the structure of different thioesters and the free energy barriers of the thiol-thioester exchange step. According to the calculation results, the thiol-thioester exchange step is disfavored by the steric hindrance around the carbonyl center, while the electronic effect (i.e. conjugation and hyper-conjugation effects) becomes important when the steric hindrance is insignificant.

Key words:

1. [1] P.E. Dawson, T.W. Muir, L.C. Lewis, S.B.H. Kent, Synthesis of proteins by native chemical ligation, Science 266(1994) 776-779.[1] P.E. Dawson, T.W. Muir, L.C. Lewis, S.B.H. Kent, Synthesis of proteins by native chemical ligation, Science 266(1994) 776-779.
2. [2] P. Thapa, R.Y. Zhang, V. Menon, et al., Native chemical ligation:a boon to peptide chemistry, Molecules 19(2014) 14461-14483.[2] P. Thapa, R.Y. Zhang, V. Menon, et al., Native chemical ligation:a boon to peptide chemistry, Molecules 19(2014) 14461-14483.
3. [3] S. Stanchev, Z. Zawada, L. Moninc ová, et al., Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern, J. Pept. Sci. 20(2014) 725-735.[3] S. Stanchev, Z. Zawada, L. Moninc ová, et al., Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern, J. Pept. Sci. 20(2014) 725-735.
4. [4] T. Nakamura, A. Shigenaga, K. Sato, et al., Examination of native chemical ligation using peptidyl prolyl thioesters, Chem. Commun. 50(2014) 58-60.[4] T. Nakamura, A. Shigenaga, K. Sato, et al., Examination of native chemical ligation using peptidyl prolyl thioesters, Chem. Commun. 50(2014) 58-60.
5. [5] H. Kawashima, T. Kuruma, M. Yamashita, et al., Synthesis of an O-acyl isopeptide by using native chemical ligation in an aqueous solvent system, J. Pept. Sci. 20(2014) 361-365.[5] H. Kawashima, T. Kuruma, M. Yamashita, et al., Synthesis of an O-acyl isopeptide by using native chemical ligation in an aqueous solvent system, J. Pept. Sci. 20(2014) 361-365.
6. [6] J.S. Zheng, S. Tang, Y.K. Qi, et al., Chemical synthesis of proteins using peptide hydrazides as thioester surrogates, Nat. Protoc. 8(2013) 2483.[6] J.S. Zheng, S. Tang, Y.K. Qi, et al., Chemical synthesis of proteins using peptide hydrazides as thioester surrogates, Nat. Protoc. 8(2013) 2483.
7. [7] H. van de Langemheen, M. van Hoeke, H.C. Quarles van Ufford, et al., Scaffolded multiple cyclic peptide libraries for protein mimics by native chemical ligation, Org. Biomol. Chem. 12(2014) 4471-4478.[7] H. van de Langemheen, M. van Hoeke, H.C. Quarles van Ufford, et al., Scaffolded multiple cyclic peptide libraries for protein mimics by native chemical ligation, Org. Biomol. Chem. 12(2014) 4471-4478.
8. [8] Y.M. Li, Y.T. Li, M. Pan, et al., Irreversible site-specific hydrazinolysis of proteins by use of sortase, Angew. Chem. Int. Ed. 53(2014) 2198-2202.[8] Y.M. Li, Y.T. Li, M. Pan, et al., Irreversible site-specific hydrazinolysis of proteins by use of sortase, Angew. Chem. Int. Ed. 53(2014) 2198-2202.
9. [9] C.T.T. Wong, C.L. Tung, X.C. Li, Synthetic cysteine surrogates used in native chemical ligation, Mol. BioSyst. 9(2013) 826-833.[9] C.T.T. Wong, C.L. Tung, X.C. Li, Synthetic cysteine surrogates used in native chemical ligation, Mol. BioSyst. 9(2013) 826-833.
10. [10] Q.Q. He, G.M. Fang, L. Liu, Design of thiol-containing amino acids for native chemical ligation at non-Cys sites, Chin. Chem. Lett. 24(2013) 265-269.[10] Q.Q. He, G.M. Fang, L. Liu, Design of thiol-containing amino acids for native chemical ligation at non-Cys sites, Chin. Chem. Lett. 24(2013) 265-269.
11. [11] L.R. Malins, N.J. Mitchell, R.J. Payne, Peptide ligation chemistry at selenol amino acids, J. Pept. Sci. 20(2014) 64-77.[11] L.R. Malins, N.J. Mitchell, R.J. Payne, Peptide ligation chemistry at selenol amino acids, J. Pept. Sci. 20(2014) 64-77.
12. [12] R.E. Thompson, X.Y. Liu, N. Alonso-García, et al., Trifluoroethanethiol:an additive for efficient one-pot peptide ligation-desulfurization chemistry, J. Am. Chem. 136(2014) 8161.[12] R.E. Thompson, X.Y. Liu, N. Alonso-García, et al., Trifluoroethanethiol:an additive for efficient one-pot peptide ligation-desulfurization chemistry, J. Am. Chem. 136(2014) 8161.
13. [13] J.S. Zheng, H.N. Chang, F.L. Wang, L. Liu, Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation, J. Am. Chem. Soc. 133(2011) 11080.[13] J.S. Zheng, H.N. Chang, F.L. Wang, L. Liu, Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation, J. Am. Chem. Soc. 133(2011) 11080.
14. [14] L.E. Canne, S.J. Bark, S.B.H. Kent, Extending the applicability of native chemical ligation, J. Am. Chem. Soc. 118(1996) 5891-5896.[14] L.E. Canne, S.J. Bark, S.B.H. Kent, Extending the applicability of native chemical ligation, J. Am. Chem. Soc. 118(1996) 5891-5896.
15. [15] P.E. Dawson, M.J. Churchill, M.R. Ghadiri, S.B.H. Kent, Modulation of reactivity in native chemical ligation through the use of thiol additives, J. Am. Chem. Soc. 119(1997) 4325-4329.[15] P.E. Dawson, M.J. Churchill, M.R. Ghadiri, S.B.H. Kent, Modulation of reactivity in native chemical ligation through the use of thiol additives, J. Am. Chem. Soc. 119(1997) 4325-4329.
16. [16] C. Wang, Q.X. Guo, Y. Fu, Theoretical analysis of the detailed mechanism of native chemical ligation reactions, Chem. Asian J. 6(2011) 1241-1251.[16] C. Wang, Q.X. Guo, Y. Fu, Theoretical analysis of the detailed mechanism of native chemical ligation reactions, Chem. Asian J. 6(2011) 1241-1251.
17. [17] Q. Zhang, H.Z. Yu, J. Shi, Orbital interactions in native chemical ligation reaction of proline thioesters, Acta. Phys. Chim. Sin. 29(2013) 2321-2331.[17] Q. Zhang, H.Z. Yu, J. Shi, Orbital interactions in native chemical ligation reaction of proline thioesters, Acta. Phys. Chim. Sin. 29(2013) 2321-2331.
18. [18] D.H. Yu, J.N. Shao, R.X. He, M. Li, Mechanism of trifluoromethylation reactions with well-defined NHC copper trifluoromethyl complexes and iodobenzene:a computational exploration, Chin Chem. Lett. 26(2015) 564.[18] D.H. Yu, J.N. Shao, R.X. He, M. Li, Mechanism of trifluoromethylation reactions with well-defined NHC copper trifluoromethyl complexes and iodobenzene:a computational exploration, Chin Chem. Lett. 26(2015) 564.
19. [19] X.N. Ke, C.M. Schienebeck, C.C. Zhou, X.F. Xu, W.P. Tang, Mechanism and reactivity of rhodium-catalyzed intermolecular[5+1] cycloaddition of 3-acyloxy-1,4-enyne (ACE) and CO:a computational study, Chin. Chem. Lett. 26(2015) 730.[19] X.N. Ke, C.M. Schienebeck, C.C. Zhou, X.F. Xu, W.P. Tang, Mechanism and reactivity of rhodium-catalyzed intermolecular[5+1] cycloaddition of 3-acyloxy-1,4-enyne (ACE) and CO:a computational study, Chin. Chem. Lett. 26(2015) 730.
20. [20] E.C.B. Johnson, S.B.H. Kent, Insights into the mechanism and catalysis of the native chemical ligation reaction, J Am. Chem. Soc. 128(2006) 6640-6646.[20] E.C.B. Johnson, S.B.H. Kent, Insights into the mechanism and catalysis of the native chemical ligation reaction, J Am. Chem. Soc. 128(2006) 6640-6646.
21. [21] H.Z. Yu, F. Fu, L. Zhang, et al., Accurate predictions of C-SO₂R bond dissociation enthalpies using density functional theory methods, Phys. Chem. Chem. Phys. 16(2014) 20964-20970.[21] H.Z. Yu, F. Fu, L. Zhang, et al., Accurate predictions of C-SO₂R bond dissociation enthalpies using density functional theory methods, Phys. Chem. Chem. Phys. 16(2014) 20964-20970.
22. [22] H.Z. Yu, Y.M. Yang, L. Zhang, Z.M. Dang, G.H. Hu, Quantum-chemical predictions of pKa's of thiols in DMSO, J. Phys. Chem. A 118(2014) 606-622.[22] H.Z. Yu, Y.M. Yang, L. Zhang, Z.M. Dang, G.H. Hu, Quantum-chemical predictions of pKa's of thiols in DMSO, J. Phys. Chem. A 118(2014) 606-622.
23. [23] M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford, CT, 2013.[23] M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford, CT, 2013.
24. [24] T.M. Hackeng, J.H. Griffin, P.E. Dawson, Protein synthesis by native chemical ligation:expanded scope by using straightforward methodology, Proc. Natl. Acad. Sci. U. S. A. 96(1999) 10068-10073.[24] T.M. Hackeng, J.H. Griffin, P.E. Dawson, Protein synthesis by native chemical ligation:expanded scope by using straightforward methodology, Proc. Natl. Acad. Sci. U. S. A. 96(1999) 10068-10073.
25. [25] J.X. Wang, G.M. Fang, Y. He, et al., Peptide o-aminoanilides as crypto-thioesters for protein chemical synthesis, Angew. Chem. Int. Ed. 54(2015) 2194.[25] J.X. Wang, G.M. Fang, Y. He, et al., Peptide o-aminoanilides as crypto-thioesters for protein chemical synthesis, Angew. Chem. Int. Ed. 54(2015) 2194.
26. [26] S.B. Pollock, S.B.H. Kent, An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation, Chem. Commun. 47(2011) 2342-2344.[26] S.B. Pollock, S.B.H. Kent, An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation, Chem. Commun. 47(2011) 2342-2344.
27. [27] C.Z. Sun, G. Luo, S. Neravetla, S.S. Ghosh, B. Forood, Native chemical ligation derived method for recombinant peptide/protein C-terminal amidation, Bioorg. Med. Chem. Lett. 23(2013) 5203-5208.[27] C.Z. Sun, G. Luo, S. Neravetla, S.S. Ghosh, B. Forood, Native chemical ligation derived method for recombinant peptide/protein C-terminal amidation, Bioorg. Med. Chem. Lett. 23(2013) 5203-5208.
28. [28] J.S. Zheng, S. Tang, Y.C. Huang, L. Liu, Development of new thioester equivalents for protein chemical synthesis, Acc. Chem. Res. 46(2013) 2475.[28] J.S. Zheng, S. Tang, Y.C. Huang, L. Liu, Development of new thioester equivalents for protein chemical synthesis, Acc. Chem. Res. 46(2013) 2475.
29. [29] T. Küh, M. Chen, K. Teichmann, A. Stark, D. Imhof, Ionic liquid 1-ethyl-3-methylimidazolium acetate:an attractive solvent for native chemical ligation of peptides, Tetrahedron Lett. 55(2014) 3658-3662.[29] T. Küh, M. Chen, K. Teichmann, A. Stark, D. Imhof, Ionic liquid 1-ethyl-3-methylimidazolium acetate:an attractive solvent for native chemical ligation of peptides, Tetrahedron Lett. 55(2014) 3658-3662.

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