The Development and Analytical Application of Gas-phase Chiral Reactions

University Of California-Davis, Davis CA

Investigators

Abstract

The project entitled "The Development and Analytical Application of Gas-phase Chiral Reactions" is directed by an established investigator with prior NSF support. Professor Carlito Lebrilla of the University of California is supported by the Analytical and Surface Chemistry program. The purpose of the research is: (1) to study the fundamental nature of the chiral specificity of gas phase ion/molecule exchange reactions (2) to optimize and quantify the exchange reaction for chiral amino acids; (3) to test the method with other classes of compounds including chiral molecules of pharmaceutical importance. The protonated amino acid-cyclodextrin complexes are stored in the homogeneous region of a 5.2 tesla superconducting magnet of a Fourier Transform Mass Spectrometer (FTMS). The positively charged complex will be allowed to undergo collisions with neutral gaseous alkylamines. The alkylamines undergo exchange reactions with the amino acids. The rate of exchange is dependent on the chirality with one enantiomer reacting at rates up to four times faster than the other enantiomer. This study will directly impact separation chemistry and mass spectrometry. The methodology developed may prove useful to industry as a rapid means for the identification of new chiral stationary phases. It may also prove useful in the pharmaceutical industry, where accurate measurement and separation of enantiomers is vital, or in process control, where speed and specificity are needed, as in the analysis of chiral libraries.