Multicomponent Aqueous Synthesis of Iodo-1,2,3-triazoles: Single-Step Models for Dual Modification of Free Peptide and Radioactive Iodo Labeling
Multicomponent Aqueous Synthesis of Iodo-1,2,3-triazoles: Single-Step Models for Dual Modification of Free Peptide and Radioactive Iodo Labeling
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Iodo-1,2,3-三唑的多组分水相合成：游离肽和放射性碘标记双重修饰的单步模型
DOI：
10.1002/chem.201605034
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发表时间：
2017-01-01
影响因子：
4.3
通讯作者：
Zhang, Guisheng
中科院分区：
文献类型：
--
作者：
Li, Lingjun;Ding, Shengqiang;Zhang, Guisheng
碘代 - 1,2,3 - 三唑在化学和生物医学应用方面备受关注。然而，目前制备碘代 - 1,2,3 - 三唑的合成方法难以轻易应用于在水中对生物活性分子进行直接修饰。通过将水相兼容的氧化碘化反应与铜催化的炔 - 叠氮环加成反应相结合，开发出了一种新型的铜催化水相多组分合成5 - 碘代 - 1,2,3 - 三唑的方法。该方法对于包括含有核苷、糖类和氨基酸部分的生物相关化合物等底物具有高效性和选择性。基于这种水相串联反应，从容易获得的起始原料出发，开发出了一种对肽进行直接一步多组分双重修饰的方法。此外，该方法还可用于以市售碘化钠（¹²⁵I）水溶液为起始原料，进行简洁快速的多组分放射性¹²⁵I标记。
Iodo-1,2,3-triazoles are of considerable interest for chemical and biomedical applications. However, current synthetic methods for preparing iodo-1,2,3-triazoles cannot easily be applied to the direct modification of bioactive molecules in water. Through the combination of water-compatible oxidative iodination and the copper-catalyzed alkyneazide cycloaddition reaction, a novel copper-catalyzed aqueous multicomponent synthetic method for the preparation of 5-iodo-1,2,3-triazoles has been developed. The method is highly effective and selective for substrates including biologically relevant compounds with nucleoside, sugar, and amino acid moieties. Based on this aqueous tandem reaction, a direct single-step multicomponent dual modification of peptide is developed from readily available starting materials. Furthermore, the method could also be applied to concise and fast multicomponent radioactive I-125 labeling from an aqueous solution of commercially available sodium (125)iodide as a starting material.