Rapid Construction of a Tyr C6–Trp C5′ Linkage: Application in the Total Synthesis of Micitide 982, a Noncanonical Cyclic Peptide
Abstract
Abstract In this study, a facile synthesis method for a highly strained Tyr C6‐to‐Trp C5′ linkage was developed. This method enables the convergent introduction of arbitrary biaryls to peptide linkers through electrochemically assisted Ni‐catalyzed cross‐electrophile coupling, followed by regioselective Larock macrocyclization. Additionally, using this approach, the total synthesis of the ribosomally synthesized and post‐translationally modified peptide (RiPP) molecule micitide 982 was accomplished. Furthermore, this synthetic strategy allows for the incorporation of various biaryls.
Article Details
Authors (5)
Hiroshige Ogawa
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, 999077 Kowloon, Hong Kong SAR, China
Yuuya Nagata
Institute for Chemical Reaction Design and Discovery (WPI-ICReDD)
Tsz Ki Chan
Department of Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon, Hong Kong SAR, China
Yudai Matsuda
Department of Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon, Hong Kong SAR, China
Hugh Nakamura
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, 999077 Kowloon, Hong Kong SAR, China