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首页> 外文期刊>Chemistry: A European journal >Imidazole-Aided Native Chemical Ligation: Imidazole as a One-Pot Desulfurization-Amenable Non-Thiol-Type Alternative to 4-Mercaptophenylacetic Acid
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Imidazole-Aided Native Chemical Ligation: Imidazole as a One-Pot Desulfurization-Amenable Non-Thiol-Type Alternative to 4-Mercaptophenylacetic Acid

机译：咪唑辅助的天然化学连接：咪唑作为4-巯基苯乙酸的一锅脱硫型非硫醇型替代品

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摘要

Various bioactive proteins have been synthesized by native chemical ligation (NCL) and its combination with subsequent desulfurization (e.g., conversion from Cys to Ala). In NCL, excess 4-mercaptophenylacetic acid (MPAA) is generally added to facilitate the reaction. However, co-elution of MPAA with the ligation product during preparative high-performance liquid chromatography sometimes reduces its usefulness. In addition, contamination of MPAA disturbs subsequent desulfurization. Here, we report for the first time that imidazole can be adopted as an alternative to MPAA in NCL using a peptide-alkylthioester. The efficiency of the imidazole-aided NCL (Im-NCL) is similar to that of traditional MPAA-aided NCL. As model cases, we successfully synthesized adiponectin(19-107) and [Ser(PO3H2)(65)]-ubiquitin using Im-NCL with a one-pot desulfurization.
机译：通过天然化学连接（NCL）及其与随后的脱硫（例如，从Cys到Ala的转化）的组合已经合成了多种生物活性蛋白。在NCL中，通常会加入过量的4-巯基苯乙酸（MPAA）以促进反应。但是，在制备型高效液相色谱过程中，MPAA与连接产物的共洗脱有时会降低其实用性。另外，MPAA的污染会干扰随后的脱硫。在这里，我们首次报道咪唑可以在NCL中使用肽-烷基硫酯替代MPAA。咪唑辅助NCL（Im-NCL）的效率类似于传统MPAA辅助NCL的效率。作为模型案例，我们使用一锅式脱硫成功地使用Im-NCL合成了脂联素（19-107）和[Ser（PO3H2）（65）]-泛素。

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