TITLE:
Determination of Enantiomeric Composition of Substituted Tetrahydroisoquinolines Based on Derivatization with Menthyl Chloroformate
AUTHORS:
Jan Přech, Václav Matoušek, Jiří Václavík, Jan Pecháček, Kamila Syslová, Petr Šot, Jakub Januščák, Beáta Vilhanová, Marek Kuzma, Petr Kačer
KEYWORDS:
Tetrahydroisoquinolines; Enantiomeric Composition; Derivatization; Menthyl Chloroformate; Gas Chromatography
JOURNAL NAME:
American Journal of Analytical Chemistry,
Vol.4 No.3,
March
27,
2013
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 (–)-(1R)-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 significantly
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.