Peptide Diversification through Addition Reaction of Free Carboxylic Acids to Ynamides
Peptide Diversification through Addition Reaction of Free Carboxylic Acids to Ynamides
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DOI：
10.3390/pr11082262
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发表时间：
2023-07
期刊：
影响因子：
3.5
通讯作者：
Zhefan Zhang;Lingchao Cai;Liangliang Song
中科院分区：
文献类型：
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作者：
Zhefan Zhang;Lingchao Cai;Liangliang Song
肽修饰已成为学术界和制药行业的一个重要课题。然而，他们主要关注胺、硫醇和醇的多样化。肽中酸残基的直接化学选择性修饰相对不发达。在这种情况下，我们报告了一种直接功能化肽中酸残基的新颖且有效的方法。通过使用炔酰胺作为反应伴侣，可以在室温下在水中以中等至优异的产率快速获得加合物。该方法显示出优异的化学选择性和广泛的范围，包括带有未保护的色氨酸或酪氨酸残基和游离的丝氨酸或谷氨酰胺残基的二肽。
Peptide modification has emerged as an important topic in the academic community and pharmaceutical industry. However, they are primarily focused on the diversification of amines, thiols, and alcohols. Direct and chemoselective modification of acid residues in peptides is relatively underdeveloped. In this context, we report a novel and efficient method for the direct functionalization of acid residues in peptides. By using ynamides as reaction partners, the adducts are rapidly obtained in moderate to excellent yields at room temperature in water. This approach shows excellent chemoselectivity and a broad scope including dipeptides bearing unprotected Trp or Tyr residue and free Ser or Gln residue.