Year: 2025
Type: article
Abstract: This study establishes an efficient solid-phase strategy for the total synthesis of segetalins A–H, J and K ( 1 – 10 ), bioactive cyclopeptides isolated from Vaccaria segetalis . Linear precursors were assembled on cost-effective 2-chlorotrityl chloride resin via Fmoc-SPPS, followed by PyBOP-mediated head-to-tail cyclization in DMF (10 −3 M). After RP-HPLC purification, all cyclopeptides were obtained in 45–70% isolated yields. Structural identities were confirmed by HRESIMS, NMR, and HPLC (>95% purity). Circular dichroism (CD) spectroscopy revealed distinct secondary structures, including β-sheets ( 1 , 2 , 3 , 4 , 7 , 8 , 10 ) and α-helical elements ( 5 , 6 ). This scalable methodology overcomes limitations of prior syntheses, enabling biological evaluation.
DOI: 10.3762/bjoc.21.202
Authors: Liangyu Liu, Wanqiu Lu, Quanping Guo, Zhaoqing Xu
Institution: Lanzhou University
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: diamond
OpenAlex ID: W4416765060