Carpenter Richard D, Verkman Alan S
Departments of Medicine and Physiology, University of California, San Francisco, Health Sciences East, Room 1246, Box 0521, 513 Parnassus Ave., San Francisco, CA 94143-0521, USA ; Department of Biomedical Engineering, University of California, Davis, Genome and Biomedical Sciences Facility, 451 Health Sciences Dr., Davis, CA 95616, USA.
European J Org Chem. 2011 Mar 1;2011(7):1242-1248. doi: 10.1002/ejoc.201001450.
Triazacryptand (TAC)-based fluorescent K sensors have broad biomedical utility, yet their advancement has been hindered because of their challenging synthesis. Herein, an efficient synthesis is reported that delivers a didesmethyl tri-azacryptand (ddTAC) K sensor in twofold fewer steps and ninefold higher overall yield than the original TAC synthesis. Our synthesis utilizes a C-O dianionic oxidative macrocyclization and reports new examples of aminoarylations and a microwave route to xanthythilium chromophores. The K sensitivity and selectivity of the ddTAC-based sensor are comparable to the TAC-based sensor.
基于三氮杂穴醚（TAC）的荧光钾离子传感器具有广泛的生物医学应用价值，然而由于其合成具有挑战性，其发展受到了阻碍。在此，我们报道了一种高效合成方法，该方法合成去二甲基三氮杂穴醚（ddTAC）钾离子传感器的步骤比原始TAC合成法减少了一半，总产率提高了九倍。我们的合成方法利用了碳-氧双负离子氧化大环化反应，并报道了氨基芳基化反应的新实例以及一种合成呫吨硫鎓发色团的微波路线。基于ddTAC的传感器对钾离子的灵敏度和选择性与基于TAC的传感器相当。
