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Chiral Separations in GC
Outline
• Introduction
• Theory
• Advantages and Disadvantages
• Applications
• Conclusions
• References
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Chiral Separations in GC
Introduction:
• One of the limitations of conventional GC
–Cannot be used to separate enantiomers.
–Enantiomers are nonsuperimposable mirror-image molecules.
–Since they have identical properties, they elute at the same time in
non-chiral GC.
• However diastereomers can be separated using
chromatography:
–Different chromatographic properties
–Different retention times
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Chiral Separations in GC
Introduction:
• Chiral separations in GC can be achieved via:
–Using a derivatization procedure with a chiral auxiliary
–Using mobile phase additive
to form diastereomer complexes which then separated on an achiral
stationary phase.
–Using a non-racemic chiral stationary phase (CSP)
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Chiral Separations in GC
Introduction:
• In the late 1960s, chiral separation in GC was a challenging problem among
scientists.
• In 1967, Prof. E. Gil-Av was successfully demonstrated chiral separation for L- and
D-amino acid esters with lauryl ester of N-trifluoroacetyl-L-isoleucine as CSP.
• In 1977, the first polysiloxane bonded CSP, Chirasil-VAL (thermal stability >
200⁰C) was developed by H. Frank, G. Nicholson and E. Bayer.
• In 1987, the first capillary column coated with cyclodextrins was invented by Prof.
W. A. Konig in cooperation with Macherey-Nagel.
• In the early of 1980s, the successful separations of o-, m-, p-xylenes and
ethylbenzene on a cyclodextrins CSP were published.
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Chiral Separations in GC
Theory:
The main purpose of chiral separations is to determine the precise
enantiomeric compositions or enantiomeric excess:
% ee = 100(R-S)/(R+S)
with R= major enantiomer
S= minor enantiomer of chiral analytes
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