Macrocyclization of Maleimide-Decorated Peptides via Late-Stage Rh(III)-Catalyzed Trp(C7) Alkenylation

• DOI: 10.1021/acs.orglett.3c00601
• Publication Date: 2023-03-31T12:35:40Z
• Authors: Yu Zhang; Shulei Hu; Yazhou Li; Yongkun Wang; Tao Yu; Qiangqiang Chen; Jiang Wang; Hong Liu
• Keywords: Maleimide; Reactivity

Here, we report a novel strategy for constructing maleimide-containing peptides and cyclic using Rh(III)-catalyzed tryptophan (Trp) (C7) alkenylation, which is challenging due to the inherent reactivity of indole benzenoid ring. This method scalable exhibits broad substrate scope. The utility this protocol could further be demonstrated by synthesis peptide conjugates with natural products amino acids as well construction maleimide-braced peptides.