JMSSJ On-line

JMSSJ On-line, Vol. 43 (1995) No. 1, pp. 97-105

Chiral Recognition in High Performance Liquid Chromatography/Atmospheric Pressure Chemical Ionization Mass Spectrometry		>> Full Text PDF >> References
*Kimio OKAMURA,^a) Yoshio SUMIDA,^a) Yasuhiro FUJIWARA,^a) Syunji TERADA,^a) Haedeuk KIM,^a) and Keiji HASHIMOTO^a)** ^a) Kyoto Pharmaceutical University (Nakautimachi 5, Misasagi, Yamashina-ku, Kyoto 607, Japan)*

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.

Key words: Chiral recognition, LC/APCIMS, 1 : 1 adduct ion, Amino acid, Optically resolving agent, X-Ray crystallography

[ Full Text PDF ] [ References ]