The New Salcylaldehyde S,S-Propanedithioacetal Ester Enables N-to-C Sequential Native Chemical Ligation and Ser/Thr Ligation for Chemical Protein Synthesis,Journal of the American Chemical Society

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The New Salcylaldehyde S,S-Propanedithioacetal Ester Enables N-to-C Sequential Native Chemical Ligation and Ser/Thr Ligation for Chemical Protein Synthesis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-04-14 , DOI: 10.1021/jacs.0c01561
Dong-Liang Huang _{1,

2} , Ying Li ₃ , Jun Liang ₁ , Lu Yu ₂ , Min Xue ₁ , Xiu-Xiu Cao ₂ , Bin Xiao ₃ , Chang-Lin Tian _{1,

2} , Lei Liu ₄ , Ji-Shen Zheng _{1,

2}

Affiliation

The combination of distinct peptide ligation techniques to facilitate chemical protein synthesis represents one of the long-standing goals in the field. A new combination ligation method of N-to-C sequential native chemical ligation and Ser/Thr ligation (NCL-STL) is described for the first time. This method relies on the peptide salcylaldehyde S,S-propanedithioacetal (SALPDT)-ester prepared by a new 1,3-propanedithiol-mediated reaction. The peptide SALPDT-ester, which is compatible with NCL, can be fully activated by N-chlorosuccinimide (NCS)/AgNO3 in aqueous solution to afford peptide SAL-ester for use in the subsequent STL. The practicality of the combined NCL-STL method is illustrated by the synthesis of S-palmitoylated matrix-2 ion channel from Influenza A virus and S-palmitoylated interferon-induced transmembrane protein 3. This approach expands the multiple-segments peptide ligation toolkit for producing important and complex custom-made protein samples by chemical protein synthesis.

中文翻译：

新的 Salcylaldehyde S,S-丙二硫缩醛酯使 N-to-C 顺序天然化学连接和用于化学蛋白质合成的 Ser/Thr 连接成为可能

结合不同的肽连接技术以促进化学蛋白质合成是该领域的长期目标之一。首次描述了一种新的 N-to-C 顺序天然化学连接和 Ser/Thr 连接 (NCL-STL) 的组合连接方法。该方法依赖于由新的 1,3-丙二硫醇介导的反应制备的肽水杨醛 S,S-丙二硫缩醛 (SALPDT)-酯。与 NCL 相容的肽 SALPDT-酯可以在水溶液中被 N-氯琥珀酰亚胺 (NCS)/AgNO3 完全活化，得到用于后续 STL 的肽 SAL-酯。结合 NCL-STL 方法的实用性通过从甲型流感病毒和 S-棕榈酰化干扰素诱导的跨膜蛋白 3 合成 S-棕榈酰化基质 2 离子通道来说明。

更新日期：2020-04-14

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