Zhang Y,
Hu S,
Li Y,
Wang Y,
Yu T,
Chen Q,
Wang J,
*,
Liu H.
*
Shanghai Institute of Materia Medica, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Beijing, China Pharmaceutical University, Nanjing, and Nanjing University of Chinese Medicine, P. R. of China
Macrocyclization of Maleimide-Decorated Peptides via Late-Stage Rh(III)-Catalyzed Trp(C7) Alkenylation.
Org. Lett. 2023;
25: 2456-2460
DOI:
10.1021/acs.orglett.3c00601
Key words
rhodium catalysis - C–H functionalization - macrocyclic peptides - tryptophan-containing peptides
Significance
Late-stage functionalization plays an inherent role in the construction of peptides and macrocyclic peptides. In the present study, the authors developed a Rh(III)-catalyzed alkenylation of tryptophan-containing peptides for the synthesis of maleimide-decorated peptides and macrocyclic peptides.
Comment
Rh(III)-catalyzed alkenylation of tryptophan-containing peptides proceeded smoothly to deliver maleimide-decorated peptides in good yields with excellent selectivity. The intramolecular reaction of maleimide-decorated peptides produced macrocyclic peptides.
