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Synthesis of enantiopure, trisubstituted cryptophane-A derivatives.

ABSTRACT: 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 (129)Xe biosensors. Hyperpolarized (129)Xe 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 (129)Xe in different biochemical environments.

SUBMITTER: Taratula O

PROVIDER: S-EPMC3484212 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Synthesis of enantiopure, trisubstituted cryptophane-A derivatives.

Taratula Olena O Kim Michael P MP Bai Yubin Y Philbin John P JP Riggle Brittany A BA Haase Danniebelle N DN Dmochowski Ivan J IJ

Organic letters 20120711 14

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 (129)Xe biosensors. Hyperpolarized (129)Xe NMR spectroscopy identified single resonances for both trisubstituted cryptopha ...[more]

PMID: 22783828

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