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

被引：16

作者：

Carpenter, Richard D. ^{[1
,2
,3
]}

Verkman, Alan S. ^{[1
,2
]}

机构：

[1] Univ Calif San Francisco, Dept Med, San Francisco, CA 94143 USA

[2] Univ Calif San Francisco, Dept Physiol, San Francisco, CA 94143 USA

[3] Univ Calif Davis, Dept Biomed Engn, Genome & Biomed Sci Facil, Davis, CA 95616 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 07期

基金：

美国国家卫生研究院;

关键词：

Biosensors; Potassium; Ionophores; Cryptands; Dianionic oxidation; OPTICAL-DETECTION; K+; STEP;

D O I：

10.1002/ejoc.201001450

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 triazacryptand (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.

引用

页码：1242 / 1248

页数：7

共 28 条

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