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Determination of Enantiomeric Composition of Substituted Tetrahydroisoquinolines Based on Derivatization with Menthyl Chloroformate
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
Laboratory of Molecular Structure Characterization, Institute of Microbiology, Academy of Sciences of the Czech Republic, Prague, Czech Republic
Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 1 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 2 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 3 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 4 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 5 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 6 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 7 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 8 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
- 9 Laboratory of Molecular Structure Characterization, Institute of Microbiology, Academy of Sciences of the Czech Republic, Prague, Czech Republic
- 10 Department of Organic Technology, Institute of Chemical Technology, Prague, Czech Republic
American Journal of Analytical Chemistry·Volume 04 (2013)·Pages 125–133·Published 27 March 2013·DOI10.4236/ajac.2013.43017
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Abstract
A method for the analysis of the optical purity of a series of chiral substituted tetrahydroisoquinolines (THIQs) was developed. The method is based on pre-column derivatization of the analytes with the derivatization reagent (–)- (1 R )-menthyl chloroformate. The derivatization reaction selectively gives diastereomeric carbamates that are resolvable on an achiral non-polar GC column. The developed technique covers variously substituted THIQs, which differ sig nificantly in volatility, steric and electronic properties. In all cases, the resolution factors ( R ) exceeded the value of 1.5. The method represents a robust way of analysis of mixtures of THIQs, which are often present in various matrixes such as body fluids, tissues and reaction mixtures.
KeywordsTetrahydroisoquinolinesEnantiomeric CompositionDerivatizationMenthyl ChloroformateGas Chromatography
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