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Issue 8, 2016
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On-line chiral analysis using the kinetic method

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Abstract

Chiral analysis of constituents in solution-phase reaction mixtures can be performed by tandem mass spectrometry using the kinetic method to determine the enantiomeric excess (ee). Simply diluting an aliquot of a reaction mixture, adjusting the pH, and adding reagents necessary to form a chiral cluster ion allows chiral analysis. The product of a stereospecific N-selective alkylation reaction, 2-(3-(2-methoxyethoxy)-5-oxo-1,6-naphthyridin-6(5H)-yl)propanoic acid, was monitored for ee during the course of reaction, and it showed the expected inversion without ee erosion. Base-catalyzed racemization of the reaction product showed the expected decrease in ee as the reaction proceeded. The base-catalyzed racemization of ibuprofen was monitored on-line, providing near real-time data on ee.

Graphical abstract: On-line chiral analysis using the kinetic method

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Publication details

The article was received on 14 Jan 2016, accepted on 09 Mar 2016 and first published on 10 Mar 2016


Article type: Paper
DOI: 10.1039/C6AN00100A
Citation: Analyst, 2016,141, 2441-2446
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    On-line chiral analysis using the kinetic method

    R. M. Bain, X. Yan, S. A. Raab, S. T. Ayrton, T. G. Flick and R. G. Cooks, Analyst, 2016, 141, 2441
    DOI: 10.1039/C6AN00100A

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