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 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.
Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104, United States.
Olena
O
Taratula
Michael P
MP
Kim
Yubin
Y
Bai
John P
JP
Philbin
Brittany A
BA
Riggle
Danniebelle N
DN
Haase
Ivan J
IJ
Dmochowski
D015374:Biosensing Techniques; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014978:Xenon / Q000737:chemistry
D011083:Polycyclic Compounds; C545484:cryptophane A; D014978:Xenon