Subscribe to RSS
DOI: 10.1055/s-0039-1691495
Backbone-Enabled Peptide Macrocyclization through Late-Stage Palladium-Catalyzed C–H Activation
This study was financially supported by the NSF of China (Grants 21778030 and 21922703 to H.W.) and by the Fundamental Research Funds for the Central Universities (Grants 14380138 and 14380138 to H.W.).Publication History
Received: 17 October 2019
Accepted after revision: 06 November 2019
Publication Date:
09 December 2019 (online)
Abstract
Peptide macrocycles are widely used in fields ranging from medicinal chemistry to materials science. Efficient chemical methods for the synthesis of cyclic peptides with novel three-dimensional structures are highly desired to facilitate the development of this unique class of compounds. However, the range of methods available for constructing peptide macrocycles is limited compared with that for small molecules. We recently developed new methods for synthesizing highly constrained cyclic peptides with C–C crosslinks through Pd-catalyzed C–H activation reactions. These methods use endogenous backbone amides as directing groups and, therefore, have the potential for use in late-stage functionalization of peptide natural products.
-
References
- 1 Gause GF, Brazhnikova MG. Nature 1944; 154: 703
- 2 White CJ, Yudin AK. Nat. Chem. 2011; 3: 509
- 3 Reguera L, Rivera DG. Chem. Rev. 2019; 119: 9836
- 4 Frost JR, Scully CC. G, Yudin AK. Nat. Chem. 2016; 8: 1105
- 5 Thakkar A, Trinh TB, Pei D. ACS Comb. Sci. 2013; 15: 120
- 6 Schramma KR, Bushin LB, Seyedsayamdost MR. Nat. Chem. 2015; 7: 431
- 7 Zhan B.-B, Li Y, Xu JW, Nie X.-L, Fan J, Jin L, Shi B.-F. Angew. Chem. Int. Ed. 2018; 57: 5858
- 8 Bauer M, Wang W, Lorion ML, Dong C, Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 6339
- 9 Lorion MM, Kaplaneris N, Son J, Kuniyil R, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 1684
- 10 Gong W, Zhang G, Liu T, Giri R, Yu JQ. J. Am. Chem. Soc. 2014; 13: 16940
- 11 Noisier AF, García J, Ionuţ IA, Albericio F. Angew. Chem. Int. Ed. 2017; 56: 314
- 12 Tang J, He YD, Chen HF, Sheng WJ, Wang H. Chem. Sci. 2017; 8: 4565
- 13 Bai Z, Cai C, Yu Z, Wang H. Angew. Chem., Int. Ed. Engl. 2018; 57: 13912
- 14 Bai Q, Bai Z, Wang H. Org. Lett. 2019; 21: 8225
- 15 Brouwer AJ, Liskamp RM. J. J. Org. Chem. 2004; 69: 3662
- 16 Brouwer AJ, Elgersma RC, Jagodzinska M, Rijkers DT. S, Liskamp RM. J. Bioorg. Med. Chem. Lett. 2008; 18: 78
- 17 Wels B, Kruijtzer JA. W, Garner KM, Adan RA. H, Liskamp RM. J. Bioorg. Med. Chem. Lett. 2005; 15: 287
- 18 Giordano C, Lucente G, Masi A, Paradisi MP, Sansonea A, Spisani S. Bioorg. Med. Chem. 2006; 14: 2642
- 19 Cheng G, Wang P, Yu J.-Q. Angew. Chem. Int. Ed. 2017; 56: 8183
- 20 Seth K, Bera M, Brochetta M, Agasti S, Das A, Gandini A, Porta A, Zanoni G, Maiti D. ACS Catal. 2017; 7: 7732
- 21 Tang J, Chen H, He Y, Sheng W, Bai Q, Wang H. Nat. Commun. 2018; 9: 3383
- 22 Zhang X, Lu G, Sun M, Mahankali M, Ma Y, Zhang M, Hua W, Hu Y, Wang Q, Chen J, He G, Qi X, Shen W, Liu P, Chen G. Nat. Chem. 2018; 10: 540