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Chiral Recognizable Host-Guest Interactions Detected by Fast-Atom Bombardment Mass Spectrometry: Application to the Enantiomeric Excess Determination of Primary Amines

Mass Spectrometry is highly sensitive, but not considered as a powerful tool for chiral analysis because of the achiral nature of the mass spectrometer. Here, we describe the new method for the enantiomeric excess (ee) determination using the host-guest chiral recognition FAB mass spectrometry. A pair of labeled/unlabeled enantiomeric crown ether host compounds (HRRRR, HSSSS-dn) is characteristically used as the host-pair reagents for the ee-determination of a given primary amine guest (G+). Based on the peak intensity ratio, I (HRRRR + G)+] / I [(HSSSS-dn + G)+], of the two diastereomeric host-guest complex ions, we can successfully determine the ee value of the amine guest within the error of ±4 % ee.

 

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