We have successfully introduced arylsulfonyloxyacetic acids with long alkyl chains as lipophilic tags to the -terminus of peptides in the final step of solid phase peptide synthesis in order to purify tagged peptides. Also, the tags allow the linear peptides to be purified by solidification after liquid–liquid extraction. Moreover, macrocyclic peptide after cyclization reaction was pre-purified easily by separating the arylsulfonate produced from tags. In this report, we described the application of this methodology to the synthesis of macrocyclic peptides such as carbetocin analogues with thioether-, amino-, ether- and ester-linkage could be derived from tagged peptides.

中文翻译：

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以芳基磺酰氧基乙酸为N端官能团合成大环肽的新方法

我们在固相肽合成的最后一步成功地将具有长烷基链的芳基磺酰氧基乙酸作为亲脂性标签引入到肽的β-末端，以纯化标记的肽。此外，标签允许在液-液萃取后通过固化来纯化线性肽。此外，通过将产生的芳基磺酸盐与标签分离，可以轻松地预纯化环化反应后的大环肽。在本报告中，我们描述了该方法在大环肽合成中的应用，例如可以从标记的肽中衍生出带有硫醚、氨基、醚和酯键的卡贝缩宫素类似物。