| 天然环肽auyuittuqamide A的全合成研究 |
| 投稿时间：2021-05-19 修订日期：2021-09-22 点此下载全文 |
| 引用本文：耿晨晨,汪甜甜,李翔,王小彦,姜云云.天然环肽auyuittuqamide A的全合成研究[J].药学实践杂志,2022,40(1):53~56,61 |
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| 基金项目:无锡市科技卫生指导性项目，锡科计（2018）255号 |
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| 中文摘要:目的 用Fmoc固相直链合成和液相环合的方法合成天然环肽auyuittuqamide A。方法 以2–氯三苯甲基氯（CTC）树脂为固相载体，1,3–二异丙基碳二亚胺（DIC）和1–羟基苯并三氮唑（HOBT）为缩合剂，9–芴基甲氧基羰基（Fmoc）保护的氨基酸，按照序列依次缩合，以三氟乙醇（TFE）作为切割试剂，获得全保护直链肽。以六氟磷酸苯并三唑–1–基–氧基三吡咯烷基磷（PyBOP）和1–羟基苯并三氮唑（HOBT）为环合试剂，全保护直链肽在二氯甲烷（DCM）溶液中环合，以三氟乙酸（TFA）为脱保护试剂，获得天然环肽auyuittuqamide A。用高效液相制备色谱进行纯化，采用HR-Q-TOF-MS, 500MHz 1H-NMR进行表征分析。结果 获得纯度大于95%的天然环肽auyuittuqamide A，总收率5.48%。结论 此法合成步骤简单，产率较高，首次建立天然环肽auyuittuqamide A的全合成方法，为auyuittuqamide A的进一步研究奠定基础。 |
| 中文关键词:auyuittuqamide A 多肽固相合成 环肽 |
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| The total synthesis of natural cyclopeptide auyuittuqamide A |
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| Abstract:Objective To synthesize the natural cyclopeptide auyuittuqamide A by Fmoc-based solid phase linear synthesis and liquid phase cyclization. Methods Using 2-chlorotriphenylmethyl chloride (CTC) resin as the solid support, 1,3-diisopropylcarbodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) as the condensing agents, 9-fluorenylmethoxycarbonyl (Fmoc) to protect amino acids were assembled in sequence, and then the linear peptide bearing the protected groups was obtained in presence of trifluoroethanol (TFE) cutting reagent. The protected linear peptide was cyclized with the aid of benzotriazole hexafluorophosphate (PyBOP) and 1-hydroxybenzotriazole (HOBt) in dichloromethane (DCM) solution, followed by trifluoroacetic acid (TFA) deprotection to obtain the cyclic peptide, auyuittuqamide A that was purified by preparative HPLC and characterized by HR-MS and 500MHz 1H-NMR. Results The purity of auyuittuqamide A was more than 95% and the total yield was 5.48%. Conclusion This method has simple synthesis steps and high yield. It is the first to establish a fully synthesis method for the natural cyclic peptide auyuittuqamide A, which lays the foundation for further research of auyuittuqamide A. |
| keywords:auyuittuqamide A solid phase peptide synthesis cyclopeptide |
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