Isomeric Cyclopropenes Exhibit Unique Bioorthogonal Reactivities
Isomeric Cyclopropenes Exhibit Unique Bioorthogonal Reactivities
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DOI：
10.1021/ja407737d
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发表时间：
2013-09-18
影响因子：
15
通讯作者：
Prescher, Jennifer A.
中科院分区：
文献类型：
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作者：
Kamber, David N.;Nazarova, Lidia A.;Prescher, Jennifer A.
生物正交化学提供了对生物分子结构和功能的巨大洞察。然而，许多流行的生物正交变换彼此不相容，限制了它们在串联多个生物分子的研究中的效用。我们确定了两个反应，可以同时用于标记生物分子在复杂的环境中：四嗪与1，3-二取代环丙烯的逆电子需求狄尔斯-阿尔德反应，和腈亚胺与3，3-二取代环丙烯的1，3-偶极环加成。值得注意的是，在这些转化中使用的环丙烯的不同之处在于单个甲基的位置。这种正交反应支架将支持监测细胞和生物体中多组分过程的努力。
Bioorthogonal chemistries have provided tremendous insight into biomolecule structure and function. However, many popular bioorthogonal transformations are incompatible with one another, limiting their utility for studies of multiple biomolecules in tandem. We identified two reactions that can be used concurrently to tag biomolecules in complex environments: the inverse electron-demand Diels-Alder reaction of tetrazines with 1,3-disubstituted cyclopropenes, and the 1,3-dipolar cycloaddition of nitrile imines with 3,3-disubstituted cyclopropenes. Remarkably, the cyclopropenes used in these transformations differ by the placement of a single methyl group. Such orthogonally reactive scaffolds will bolster efforts to monitor multicomponent processes in cells and organisms.