A reproducible, highly efficient, and racemization-free protocol for the triphosgene-mediated solid-phase coupling of proteinogenic amino acids was developed. The efficiency of the reaction was demonstrated by the first total synthesis of the bioactive natural octacyclopeptide brachystemin A. This protocol will broaden the application of triphosgene in the synthesis of a wide range of peptides, including aromatic amino acids, N-alkylated amino acids, as well as proteinogenic amino acids.
Independent Research Program of the Chinese Academy of Sciences [KSCX2-EW-J-24]
; National Natural Science Foundation of China [31270273, 31070192, 30770167]
; Basic Research Program from the Ministry of Science and Technology of China [2007FY110100]
1.Chinese Acad Sci, Shenzhen Inst Adv Technol, Inst Biomed & Biotechnol, Guangdong Key Lab Nanomed, Shenzhen 518055, Guangdong, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China
Fang,Lijing;Wu,Chunlei;Yu,Zaidan;Shang,Peng;Cheng,Yongxian;Peng,Yuefeng;Su,Wu.Triphosgene-Mediated Couplings in the Solid Phase: Total Synthesis of Brachystemin A,EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2014,67(3):238-249