Synthesis of tyrocidine A and its analogues by spontaneous cyclization in aqueous solution.
[reaction: see text] Head-to-tail cyclization of peptides is a multistep process involving tedious C-terminal activation and side chain protection. Here we report a facile, quantitative cyclization method in aqueous ammonia solution for the total syntheses of the cyclic decapeptide antibiotic Tyrocidine A and its analogues from their fully deprotected linear thioester precursors on a solid support. This novel aqueous method is conformation-dependent and may be applicable to syntheses of other natural cyclic peptides.
Bu
Xianzhang
X
Department of Chemistry and Biotechnology Research Institute, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
Wu
Xiaoming
X
Xie
Guiyang
G
Guo
Zhihong
Z
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D003500:Cyclization; D010456:Peptides, Cyclic / Q000138:chemical synthesis; D012996:Solutions; D013438:Sulfhydryl Compounds / Q000737:chemistry; D014440:Tyrocidine / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D010456:Peptides, Cyclic; D012996:Solutions; D013438:Sulfhydryl Compounds; D014440:Tyrocidine