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Rapid separations of diacyl‐ and dialkylglycerol enantiomers by high performance liquid chromatography on a chiral stationary phase
Author(s) -
Takagi Toru,
Itabashi Tutaka
Publication year - 1987
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02537287
Subject(s) - enantiomer , chemistry , elution , chromatography , phase (matter) , chiral column chromatography , high performance liquid chromatography , alkyl , chiral derivatizing agent , silica gel , organic chemistry
Rapid and practical separations of 1,2‐and 2,3‐diacyl‐and dialkyl‐ sn ‐glycerol enantimers as their 3,5‐dinitrophenylurethane derivatives were carried out by normal‐phase high performance liquid chromatography on a chiral stationary phase, N‐( R )‐1‐(α‐naphthyl)ethylaminocarbonyl‐( S )‐valine chemically bonded to γ‐aminopropyl silanized silica. Complete separations of the racemates into enantiomers were achieved for both of the diacyl‐and dialkylglycerols within 10 min using a stainless steel column (25 cm long) packed with the 5‐μ particles, an isocratic elution with a mixture of hexane/ethylene dichloride/ethanol as a mobile phase and a UV detector. The sn ‐1,2‐enantiomers were eluted ahead of the corresponding sn ‐2,3‐enantiomers. Satisfactory separation of the sn ‐1,3‐diacylglycerols from the corresponding enantiomers and the separation of the homologues differing in acyl and alkyl groups were also observed. The formations of hydrogen bonding and charge transfer complex between the urethane derivatives and the stationary phase may contribute to the enantiomer separations.