Total Synthesis and Biological Evaluation of PF1171A, C, F, and G, Cyclic Hexapeptides with Insecticidal Activity

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• 作者：Yuichi Masuda ; Ren Tanaka ; Kenji Kai ; A. Ganesan ; Takayuki Doi
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：September 5, 2014
• 年：2014
• 卷：79
• 期：17
• 页码：7844-7853
• 全文大小：494K
• ISSN：1520-6904

文摘

The total synthesis of the cyclic hexapeptides PF1171A, C, F, and G has been achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The synthesis includes a solid-phase peptide coupling with the weakly nucleophilic amino group of an anthranilic acid residue. This was efficiently achieved by in situ generation of an Fmoc-amino acid chloride using triphosgene. The natural products exhibit potent paralytic activities against silkworm larvae, whereas epi-PF1171A and epi-PF1171C, bearing l-Ala instead of d-Ala, were relatively inactive. X-ray crystallographic analysis indicates that intramolecular hydrogen bonds in PF1171 peptides are critical for maintaining their active conformations.