Department of Chemistry and Howard Hughes Medical Institute, University of California, Berkeley, California 94720, USA.
J Am Chem Soc. 2010 Mar 24;132(11):3688-90. doi: 10.1021/ja100014q.
Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. The reaction of azides with strained alkynes, such as cyclooctynes, readily forms a triazole product without the need for a toxic catalyst. Here we describe a biarylazacyclooctynone (BARAC) that has exceptional reaction kinetics and whose synthesis is designed to be both modular and scalable. We employed BARAC for live cell fluorescence imaging of azide-labeled glycans. The high signal-to-background ratio obtained using nanomolar concentrations of BARAC obviated the need for washing steps. Thus, BARAC is a promising reagent for in vivo imaging.
生物正交化学反应是指不会与生物相互作用或干扰的化学反应，它使得人们能够探索许多以前难以研究的生物学过程。叠氮化物与张力炔烃（如环辛炔）的反应很容易形成三唑产物，而不需要有毒的催化剂。在这里，我们描述了一种具有出色反应动力学的双芳基氮杂环辛炔（BARAC），其合成设计既具有模块性又具有可扩展性。我们使用 BARAC 对叠氮标记的聚糖进行活细胞荧光成像。使用纳摩尔浓度的 BARAC 获得的高信噪比消除了洗涤步骤的需要。因此，BARAC 是一种有前途的体内成像试剂。
