The stereospecific ion-molecule reaction between optically resolving agents (a pair of enantiomers of mandelic acid, methyl mandelate, and 1-phenylethylamine) and several enantiomers of amino acids were investigated by high performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry (HPLC/APCIMS). On the APCI mass spectra, the 1 : 1 adduct ion [M…H…X]+ that the amino acid molecule [M] reacted with the protonated optically resolving agent in mobile phase [XH]+ has been prominently observed. The results show that the relative abundances of 1 : 1 adduct ions [M…H…X]+ formed from samples (amino acids) and reagents (resolving agent) of the same configuration (homo-chiral) are much higher than those of different configurations (hetero-chiral). To support this hypothesis, we carried out X-ray crystallographic analysis on diastereomeric complexes of (S)-phenylalanine with (R)- and (S)-mandelic acid for a resolving agent as a model compound. The crystal structure obtained was in accordance with the stereochemical effects observed in APCIMS.
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Okamura et al. (1995) studied this question.
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