Methods of structural determination for molecules carrying chiral center(s) are important to understanding biological function(s) of such molecules. Mass Spectrometry (MS) is of particular importance in these days because of high sensitivity. This indispensible analytical method, however, is known to be �chiral blind�.In this study, chiral auxiliary groups were introduced into enantiomers producing a pair of diastereomers, which were then analyzed by means of energy-resolved mass spectrometry (ERMS). Here, we focused decay of precursor ions, which reflects energies required for dissociation of chemical bonds and/or adducted metal ion species.Consequently, it was shown that discrimination of a series of diastereomers, which were obtained by incorporating chiral auxiliary groups, was possible. It was considered that steric impediments of bulky groups present at both stereocenters lead to the energy difference. These findings suggest a possibility of determining absolute configuration of a chiral compound based on MS only without using standard compounds.

Challenge to determining absolute configuration based on mass spectrometry with the aid of chiral auxiliary group

243rd National Meeting (2012)

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