Solid‐phase synthesis and bioactivity evaluation of cherimolacyclopeptide E,Journal of Peptide Science

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Solid‐phase synthesis and bioactivity evaluation of cherimolacyclopeptide E
Journal of Peptide Science ( IF 1.8 ) Pub Date : 2021-02-15 , DOI: 10.1002/psc.3308
Yuka Yoshida ₁ , Minoru Inagaki ₁ , Yuichi Masuda ₁

Affiliation

Cherimolacylopeptide E (1) is a cyclic hexapeptide isolated from the seeds of Annona cherimola. Peptide 1 reportedly exhibits potent cytotoxicity against KB cells (IC₅₀ 0.017 μM). To confirm the structure and bioactivity of 1, we conducted a total synthesis of its proposed structure. The synthesis was accomplished via solid‐phase peptide elongation and macrocyclization by employing Fmoc/OAll‐protected amino acids on 2‐Cl‐trityl resin. NMR analysis revealed that synthetic 1 exists in two conformations in pyridine‐d₅. As the spectroscopic data of the major conformer of synthetic 1 were consistent with those of natural 1, the structure of cherimolacyclopeptide E was confirmed to be 1. However, our synthetic 1 exhibited low cytotoxicity against KB cells (IC₅₀ > 100 μM). In contrast to previously‐reported findings, our synthetic 1 exhibited little antibacterial activity against Escherichia coli.

中文翻译：

化学环肽E的固相合成及生物活性评价

Cherimolacylopeptide E ( 1 ) 是从番荔枝种子中分离得到的环状六肽。据报道，肽1对 KB 细胞显示出有效的细胞毒性 (IC ₅₀ 0.017 μM)。以确认的结构和生物活性1，我们进行了其提出的结构的全合成。通过在 2-Cl-三苯甲基树脂上使用 Fmoc/OAll 保护的氨基酸，通过固相肽延伸和大环化完成合成。核磁共振分析表明合成1在吡啶-d _{5 中}以两种构象存在。由于合成1的主要构象异构体的光谱数据与天然由图1可知，化学环肽E的结构为1。然而，我们的合成1对 KB 细胞表现出低细胞毒性（IC ₅₀ > 100 μM）。与之前报道的发现相反，我们合成的1对大肠杆菌几乎没有抗菌活性。

更新日期：2021-02-15

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