The synthesis of α-amino thioacids and peptide thioacids and their applications in chemoselective amide bond formation, ligation of peptides/proteins/glycopeptides and synthesis of peptidomimetics are reviewed. A variety of successful methods including both C-terminal and N-terminal activations for the coupling of α-amino thioacids and peptide thioacids have ascertained the thioacid-based protocol as a benign alternative to some of the traditional methods of amide/peptide bond formation which employs carboxyl activation. In addition to the couplings involving unprotected peptide fragments and solid phase synthesis, their use in the synthesis of different classes of peptidomimetics such as thioxopeptides, imide conjugates and acylsulfonamide–peptide conjugates only illustrates the versatility of this functionality in generating diverse classes of molecules, some of which are relevant to drug discovery and chemical biology. A note on more reactive seleno counterparts of thioacids, which can be useful in selective cases, is provided.

中文翻译：

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硫代酸–用于酰胺键形成和连接反应的合成子：肽和拟肽的组装

综述了α-氨基硫代酸和肽硫代酸的合成及其在化学选择性酰胺键形成，肽/蛋白质/糖肽的连接和拟肽合成中的应用。各种成功的方法，包括用于偶联α-氨基硫代酸和肽硫代酸的C端和N端活化，已经确定了基于硫代酸的方案可以作为某些传统的酰胺/肽键形成方法的良性替代方法，采用羧基活化。除了涉及未保护的肽片段和固相合成的偶联以外，它们还用于合成不同种类的拟肽，例如thioxopeptides，酰亚胺共轭物和酰磺酰胺-肽共轭物仅说明了这种功能在生成各种分子类别中的多功能性，其中有些与药物发现和化学生物学有关。提供了有关更具反应性的硫代硒酸的硒代对应物的注释，该注释在某些情况下可能有用。