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Synthesis of Enantiopure, Trisubstituted Cryptophane-A Derivatives

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Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104, United States
Cite this: Org. Lett. 2012, 14, 14, 3580–3583
Publication Date (Web):July 11, 2012
Copyright © 2012 American Chemical Society

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    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.

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    Experimental procedures and characterization data for all synthesized compounds, ECD and 129Xe NMR data. This material is available free of charge via the Internet at

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