Haiber Lisa Maria, Kufleitner Markus, Wittmann Valentin
Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), University of Konstanz, Konstanz, Germany.
Front Chem. 2021 Apr 13;9:654932. doi: 10.3389/fchem.2021.654932. eCollection 2021.
The inverse electron-demand Diels-Alder (IEDDA or DA) reaction is an emerging bioorthogonal ligation reaction that finds application in all areas of chemistry and chemical biology. In this review we highlight its application in metabolic glycoengineering (MGE). MGE is a versatile tool to introduce unnatural sugar derivatives that are modified with a chemical reporter group into cellular glycans. The IEDDA reaction can then be used to modify the chemical reporter group allowing, for instance, the visualization or isolation of glycoconjugates. During the last years, many different sugar derivatives as well as reporter groups have been published. These probes are summarized, and their chemical and biological properties are discussed. Furthermore, we discuss examples of MGE and subsequent IEDDA reaction that highlight its suitability for application within living systems.
逆电子需求狄尔斯-阿尔德（IEDDA或DA）反应是一种新兴的生物正交连接反应，在化学和化学生物学的各个领域都有应用。在本综述中，我们重点介绍其在代谢糖工程（MGE）中的应用。MGE是一种通用工具，可将用化学报告基团修饰的非天然糖衍生物引入细胞聚糖中。然后，IEDDA反应可用于修饰化学报告基团，例如实现糖缀合物的可视化或分离。在过去几年中，已经发表了许多不同的糖衍生物以及报告基团。本文对这些探针进行了总结，并讨论了它们的化学和生物学性质。此外，我们还讨论了MGE及后续IEDDA反应的实例，突出了其在活系统中应用的适用性。
