Studies on 2-Formylphenylboronic Acid-Based Ser/Thr Ligation and Cys/Pen Ligation†,Chinese Journal of Chemistry

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Studies on 2-Formylphenylboronic Acid-Based Ser/Thr Ligation and Cys/Pen Ligation†
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2021-06-30 , DOI: 10.1002/cjoc.202100385
Zhenquan Sun ₁ , Xuechen Li ₁

Affiliation

Developing an effective chemoselective ligation strategy for assembling unprotected peptide segments is important to peptide/protein synthesis. The ligation efficiency and selectivity depend on the chemistry between the C-terminal active ester of the peptide (e.g., the thioester in Native Chemical Ligation or the salicylaldehyde ester in Ser/Thr Ligation and Cys/Pen Ligation) and N-terminal functional groups of the second peptide (Cys or Ser/Thr). Increasing the reactivity of the ligation and decreasing the hydrolysis of the active ester are more like the opposite sites in balance. We investigated the potential application of the peptide acyl ester of 2-formylphenylboronic acid (2-FPBA) in the Ser/Thr ligation and Cys/Pen ligation. With the assistance of boronic acid group, the peptidyl FPBA ester showed remarkable stability in aqueous buffer and its reactivity towards Ser/Thr and Cys/Pen also improved. However, the strong coordination of the amine at the N-terminus and boronic acid suppressed the acyl transfer process when the peptide acyl group was used. More effects should be made to enhance the ligation chemistry.

中文翻译：

基于 2-甲酰基苯基硼酸的 Ser/Thr 连接和 Cys/Pen 连接的研究†

开发用于组装未受保护的肽段的有效化学选择性连接策略对于肽/蛋白质合成很重要。连接效率和选择性取决于肽的 C 端活性酯（例如.、天然化学连接中的硫酯或 Ser/Thr 连接和 Cys/Pen 连接中的水杨醛酯）和第二个肽（Cys 或 Ser/Thr）的 N 端官能团。增加连接的反应性和减少活性酯的水解更像是平衡的相反位点。我们研究了 2-甲酰基苯基硼酸 (2-FPBA) 肽酰基酯在 Ser/Thr 连接和 Cys/Pen 连接中的潜在应用。在硼酸基团的帮助下，肽基 FPBA 酯在水性缓冲液中表现出显着的稳定性，其对 Ser/Thr 和 Cys/Pen 的反应性也有所提高。然而，当使用肽酰基时，N-末端胺和硼酸的强配位抑制了酰基转移过程。

更新日期：2021-06-30

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