Abstract

European Journal of Mass Spectrometry
Volume 5 Issue 6, Pages 485–488 (1999)
doi: 10.1255/ejms.312

Chiral recognition and the determination of optical purity of a-phenylethylamine using monosaccharide as a chiral selector under liquid secondary ion mass spectral conditions

P. Krishna, S. Prabhakar and M. Vairamani^*
National Centre for Mass Spectrometry, Indian Institute of Chemical Technology, Hyderabad-500 007, India. E- mail: vairamani@iict.ap.nic.in
M. Manoharan and E.D. Jemmis
School of Chemistry, University of Hyderabad, Hyderabad-500 046, India

Naturally available monosaccharides, D-mannose, D-galactose and D-glucose, have been used for the first time as chiral co-matrices for chiral recognition of α- phenylethylamine. The liquid secondary ion (LSI) mass spectra of a mixture of D-mannose and (R)- or (S)-α-phenylethylamine in the presence of benzylamine as reference compound and glycerol as matrix showed [(mannose + (R)- / (S)-α-phenylethylamine + H)–H₂O]⁺ (a) and [(mannose + benzylamine + H)–H₂O]⁺ (b) ions. The significant difference was observed in the relative peak intensity (RPI) values calculated from the ion abundances of ion a and b. The RPI values for (R)- and (S)- α-phenylethylamine are RPI_R = 0.79 and RPI_S = 1.34, respectively. The efficiency of the chiral recognition property of D-mannose is demonstrated in estimating the enantiomeric excess of α-phenylethylamine.

Keywords: LSIMS, chiral recognition, monosaccharide, a-phenylethylamine, RPI method, enantiomeric excess

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