期刊
ORGANIC LETTERS
卷 23, 期 3, 页码 716-721出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03940
关键词
-
资金
- Natural Science Foundation of China [21672105, 21725204, 91753124]
- Fundamental Research Funds for the Central Universities (Nankai University) [63191515, 63191318, NCC2020FH02]
New methods have been developed in this study to construct peptide macrocycles via radical-mediated intramolecular C-H alkylation reactions under photoredox catalysis, providing a new strategy for the synthesis of complex peptide macrocycles.
Enzyme-catalyzed radical-mediated C-H functionalization reactions allow nature to create natural products of unusual three-dimensional structures from simple linear peptide precursors. In comparison, chemist's ability to harness radical C-H functionalization reactions for synthesis of complex peptides remains limited. In this work, new methods have been developed to construct peptide macrocycles via radical-mediated intramolecular C-H alkylation reactions under photoredox catalysis. Linear peptide precursors equipped with a C-terminal N-(acyloxy)phthalimide ester can cyclize with the alpha C-H bond of N-terminal glycine or aryl C-H bond of N-heteroarene capping units in high yield and selectivity under mild conditions. The strategy uses the C-H cyclization step to incorporate lysine, homolysine, and various heteroarene-derived amino acid linchpins into peptide macrocycles, enabling convergent and flexible synthesis of complex peptide macrocycles from simple building blocks.
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