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European J Org Chem. 2011 Mar 1;2011(7):1242-1248.

Function-Oriented Synthesis of a Didesmethyl Triazacryptand Analogue for Fluorescent Potassium Ion Sensing.

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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.


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.


Biosensors; Cryptands; Dianionic oxidation; Ionophores; Potassium

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