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

European J Org Chem

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 Heal

Published: March 2011


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Article Abstract

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3729919PMC
http://dx.doi.org/10.1002/ejoc.201001450DOI Listing

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