title: Enantioseparation of hydroxyeicosatetraenoic acids by hydroxypropyl-γ-cyclodextrin-modified micellar electrokinetic chromatography.
abstract: 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.
authors.affiliation: School of Science, Tokai University, Hiratsuka, Kanagawa, Japan.
authors.forename: Shuji
authors.initials: S
authors.lastname: Kodama
authors.affiliation: Faculty of Fisheries Sciences, Hokkaido University, Hakodate, Hokkaido, Japan.
authors.forename: Shota
authors.initials: S
authors.lastname: Nakajima
authors.affiliation: Faculty of Fisheries Sciences, Hokkaido University, Hakodate, Hokkaido, Japan.
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Ozaki
authors.affiliation: Faculty of Fisheries Sciences, Hokkaido University, Hakodate, Hokkaido, Japan.
authors.forename: Ryota
authors.initials: R
authors.lastname: Takemoto
authors.affiliation: Faculty of Fisheries Sciences, Hokkaido University, Hakodate, Hokkaido, Japan.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Itabashi
authors.affiliation: Banting and Best Department of Medical Research, University of Toronto, Toronto, ON, Canada.
authors.forename: Arnis
authors.initials: A
authors.lastname: Kuksis
mesh_terms: D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D006893:Hydroxyeicosatetraenoic Acids / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D016014:Linear Models; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D047408:gamma-Cyclodextrins / Q000737:chemistry*
chemical_list: D006893:Hydroxyeicosatetraenoic Acids; D047408:gamma-Cyclodextrins; C479659:hydroxypropyl-gamma-cyclodextrin
keywords: Enantioseparation; Gracilaria; Hydroxyeicosatetraenoic acid; Hydroxypropyl-γ-cyclodextrin; Micellar electrokinetic chromatography