Synthesis of Enantiopure, Trisubstituted Cryptophane-A Derivatives

The efficient synthesis of enantiopure, trisubstituted cryptophane-A derivatives, organic host molecules with unusually high xenon affinity, is reported. Synthesis and chromatographic separation of (±) tri-Mosher’s acid substituted cryptophane diastereomers gave ready access to the enantiopure crypt...

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Bibliographic Details
Published in:Organic letters 2012-07, Vol.14 (14), p.3580-3583
Main Authors: Taratula, Olena, Kim, Michael P, Bai, Yubin, Philbin, John P, Riggle, Brittany A, Haase, Danniebelle N, Dmochowski, Ivan J
Format: Article
Language:English
Subjects:
Biosensing Techniques
Magnetic Resonance Spectroscopy
Molecular Structure
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Stereoisomerism
Xenon - chemistry
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Summary:The efficient synthesis of enantiopure, trisubstituted cryptophane-A derivatives, organic host molecules with unusually high xenon affinity, is reported. Synthesis and chromatographic separation of (±) tri-Mosher’s acid substituted cryptophane diastereomers gave ready access to the enantiopure cryptophanes, which are critical components in the design of enantiomerically pure 129Xe biosensors. Hyperpolarized 129Xe NMR spectroscopy identified single resonances for both trisubstituted cryptophane diastereomers that were separated by 9.5 ppm. This highlights opportunities for using enantiopure xenon biosensors in the simultaneous detection of 129Xe in different biochemical environments.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300943w