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Updated: May 2, 2026
Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
Efficient solid-phase synthesis and structural characterization of segetalins A-H, J and K
Liangyu Liu1, Wanqiu Lu1, Quanping Guo1
1Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou 730000, China.
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.
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