Abstract

The developments of our quantitative chiral recognition studies in the host-guest complexations between chiral crown ethers and chiral amino acid esters by FAB, ESI, and MALDI mass spectrometry have been described. Both the enantiomer labeled (EL)-guest method and the EL-host method, which had been previously proposed by us, were successfully advanced. The relative peak intensity (IRIS) values of the diastereomeric host-guest complex ions appeared in mass spectra were especially noted, and their use to chiral recognition was illustrated. Generally, the former method was used to chiral recognition ability-determination of a given host, and the latter one was used to enantiomeric excess (e.e.)-determination of a given guest. Through the manuscript, emphasis has been put on the finding that one can detect correctly the concentration ratio of the two diastereomeric host-guest complex ions formed in a matrix solution by FAB mass spectrometry and then, that FABMS is a powerful tool for detecting chiral host-guest interactions in the host-guest complexation systems. Recent ,e.e.-determination methods by ESI mass spectrometry etc. were also summarized.

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