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Enantioseparation of hydroxyeicosatetraenoic acids by hydroxypropyl‐γ‐cyclodextrin‐modified micellar electrokinetic chromatography
Author(s) -
Kodama Shuji,
Nakajima Shota,
Ozaki Hiromichi,
Takemoto Ryota,
Itabashi Yutaka,
Kuksis Arnis
Publication year - 2016
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.201600213
Subject(s) - enantiomer , chemistry , chromatography , micellar electrokinetic chromatography , cyclodextrin , resolution (logic) , stereochemistry , electrophoresis , artificial intelligence , computer science
Complete resolution of hydroxyeicosatetraenoic acid (HETE) enantiomers was achieved using hydroxypropyl‐γ‐cyclodextrin (HP‐γ‐CD)‐modified MEKC. The optimum running conditions were determined to be utilizing a 30 mM phosphate–15 mM borate buffer (pH 9.0) containing 30 mM HP‐γ‐CD and 75 mM SDS as the BGE, application of +30 kV as the effective voltage, and carrying out the experiment at 15°C. The eluents were detected at 235 nm. The method was used successfully for the simultaneous separations of ( S )‐ and ( R )‐enantiomers of regioisomeric 8‐, 11‐, 12‐, and 15‐HETEs. Subsequently, the optimized method was applied to evaluate the stereochemistry of 8‐ and 12‐HETEs from the marine red algae, Gracilaria vermiculophylla and Gracilaria arcuata , respectively. The 8‐HETE was found to be a mixture of 98% ( R )‐enantiomer and 2% ( S )‐enantiomer, while the 12‐HETE was a mixture of 98% ( S )‐enantiomer and 2% ( R )‐enantiomer. The present study demonstrates that the HP‐γ‐CD‐modified MEKC method is simple and sensitive and provides unambiguous information on the configuration of natural and synthetic HETEs.