Development of aspartic acid ligation for peptide cyclization derived from serine/threonine ligation

doi:10.1016/j.cclet.2018.03.012

Abstract
Figure/Table
References (0)
Related Citation (8)

Download: PDF (925 KB) HTML ( )
Export: BibTeX | EndNote (RIS)

Guide Based on a mechanism analogous to the serine/threonine ligation, the aspartic acid ligation, which is facilitated by the γ-amino alcohol based ligation and oxidation, is developed and applied to the synthesis of cyclic peptides. The γ-hydroxyl group triggers the ring-chain tautomerization via a 6-endo-trig process, while the δ-hydroxyl group facilitates the oxidative cleavage of the vicinal diol to give carboxylic acid.

Abstract Based on a mechanism analogous to the serine/threonine ligation, the aspartic acid ligation, which is facilitated by the γ-amino alcohol based ligation and oxidation, is developed and applied to the synthesis of cyclic peptides. The γ-hydroxyl group triggers the ring-chain tautomerization via a 6-endo-trig process, while the δ-hydroxyl group facilitates the oxidative cleavage of the vicinal diol to give carboxylic acid.

Key words： Aspartic acid ligation Peptide cyclization Serine/threonine ligation Ring-chain tautomerization Acyl transfer Selective oxidation

Received: 13 February 2018

Fund:This work was supported by the Research Grants Council (Nos. 17309616, C6009-15G) of Hong Kong, The National Science Foundation of China (Nos. 21672180, 91753101), the Area of Excellence Scheme of the University of Grants Committee of Hong Kong (No. AoE/P-705/16).

Corresponding Authors: Xuechen Li, xuechenl@hku.hk E-mail: xuechenl@hku.hk

	Service

	E-mail this article
	Add to my bookshelf
	Add to citation manager
	E-mail Alert
	RSS
	Articles by authors

Cite this article:

URL:

http://www.chinchemlett.com.cn/EN/10.1016/j.cclet.2018.03.012 OR http://www.chinchemlett.com.cn/EN/Y2018/V29/I07/1119

[1]	Y.S. Ong, L. Gao, K.A. Kalesh, et al., Curr. Top. Med. Chem. 17(2017) 2302-2318.
[2]	A.T. Bockus, C.M. McEwen, R.S. Lokey, Curr. Top. Med. Chem. 13(2013) 821-836.
[3]	S.H. Joo, Biomol. Ther. 20(2012) 19-26.
[4]	C.J. White, A.K. Yudin, Nat. Chem. 3(2011) 509-524.
[5]	Z.M. Wu, S.Z. Liu, X.Z. Chen, et al., Chin. Chem. Lett. 27(2016) 1731-1739.
[6]	G.K.T. Nguyen, C.T.T. Wong, J. Biochem. Chem. Sci. 2017(2017) 1-13.
[7]	P.E. Dawson, T.W. Muir, I. Clark-Lewis, et al., Science 266(1994) 776-779.
[8]	P.E. Dawson, S.B.H. Kent, Annu. Rev. Biochem. 69(2000) 923-960.
[9]	G.M. Fang, Y.M. Li, F. Shen, et al., Angew. Chem. Int. Ed. 50(2011) 7645-7649.
[10]	S. Tang, J.S. Zheng, K. Yang, et al., Acta Chim. Sin. 70(2012) 1471-1476.
[11]	J.X. Wang, G.M. Fang, Y. He, et al., Angew. Chem. Int. Ed. 54(2015) 2194-2198.
[12]	K. Jin, T. Li, H.Y. Chow, et al., Angew. Chem. Int. Ed. 56(2017) 14607-14611.
[13]	C.F. Liu, J.P. Tam, J. Am. Chem. Soc. 116(1994) 4149-4153.
[14]	P. Botti, T.D. Pallin, J.P. Tam, J. Am. Chem. Soc. 118(1996) 10018-10024.
[15]	J.W. Bode, Acc. Chem. Res. 50(2017) 2104-2115.
[16]	F. Rohrbacher, G. Deniau, A. Luther, et al., Chem. Sci. 6(2015) 4889-4896.
[17]	T. Fukuzumi, L. Ju, J.W. Bode, Org. Biomol. Chem. 10(2012) 5837-5844.
[18]	R. Kleineweischede, C.P.R. Hackenberger, Angew. Chem. Int. Ed. 47(2008) 5984-5988.
[19]	C.L. Tung, C.T.T. Wong, X. Li, Org. Biomol. Chem. 13(2015) 6922-6926.
[20]	D.Y. Jackson, J.P. Burnier, J.A. Wells, J. Am. Chem. Soc. 117(1995) 819-820.
[21]	G.K.T. Nguyen, S. Wang, Y. Qiu, et al., Nat. Chem. Biol. 10(2014) 732-738.
[22]	G.K.T. Nguyen, Y. Qiu, Y. Cao, et al., Nat. Protoc. 11(2016) 1977-1988.
[23]	G.K.T. Nguyen, X. Hemu, J.P. Quek, et al., Angew. Chem. Int. Ed. 55(2016) 12802-12806.
[24]	Z.M. Wu, S.Z. Liu, X.Z. Cheng, et al., Chin. Chem. Lett. 28(2017) 553-557.
[25]	X. Li, H.Y. Lam, Y. Zhang, C.K. Chan, Org. Lett. 12(2010) 1724-1727.
[26]	Y. Zhang, C. Xu, H.Y. Lam, et al., Proc. Natl. Acad. Sci. U. S. A. 110(2013) 6657-6662.
[27]	C.T.T. Wong, T. Li, H.Y. Lam, et al., Front. Chem. 2(2014), doi:http://dx.doi.org/10.3389/fchem.2014.00028.
[28]	C.L. Lee, X. Li, Curr. Opin. Chem. Biol. 22(2014) 108-114.
[29]	C.L. Lee, X. Li, Sci. China Chem. 59(2016) 1061-1064.
[30]	H. Liu, X. Li, Org. Biomol. Chem. 12(2014) 3768-3773.
[31]	Y. Zhang, T. Li, X. Li, Org. Biomol. Chem. 11(2013) 5584-5587.
[32]	C. Xu, H.Y. Lam, Y. Zhang, et al., Chem. Commun. 49(2013) 6200-6202.
[33]	T. Li, H. Liu, X. Li, Org. Lett. 18(2016) 5944-5947.
[34]	C.L. Lee, H. Liu, C.T.T. Wong, et al., J. Am. Chem. Soc. 138(2016) 10477-10484.
[35]	C.L. Lee, H.Y. Lam, X. Li, Nat. Prod. Rep. 32(2015) 1274-1279.
[36]	H.Y. Lam, Y. Zhang, H. Liu, et al., J. Am. Chem. Soc. 135(2013) 6272-6279.
[37]	D. Lin, H.Y. Lam, W. Han, et al., Bioorg. Med. Chem. Lett. 27(2017) 456-459.
[38]	K. Jin, I.H. Sam, K.H.L. Po, et al., Nat. Commun. 7(2016) 12394.
[39]	K. Jin, K.H.L. Po, S. Wang, et al., Bioorg. Med. Chem. 25(2017) 4990-4995.
[40]	C.T.T. Wong, H.Y. Lam, X. Li, Tetrahedron 70(2014) 7770-7773.
[41]	C.T.T. Wong, H.Y. Lam, X. Li, Org. Biomol. Chem. 11(2013) 7616-7620.
[42]	C.T.T. Wong, H.Y. Lam, T. Song, et al., Angew. Chem. Int. Ed. 52(2013) 10212-10215.
[43]	J.F. Zhao, X.H. Zhang, Y.J. Ding, et al., Org. Lett. 15(2013) 5182-5185.
[44]	T. Fukuyama, S.C. Lin, L. Li, J. Am. Chem. Soc. 112(1990) 7050-7051.
[45]	Y. Yoshimura, C. Ohara, T. Imahori, et al., Bioorg. Med. Chem. 16(2008) 8273-8286.