title: Enantiomeric separation by MEKC using dodecyl thioglycoside surfactants: importance of an equatorially oriented hydroxy group at C-2 position in separation of dansylated amino acids.
abstract: To investigate the influence of stereogenic centers of sugar-based surfactants for enantiomeric separation, four n-dodecyl thioglycoside sulfates (CMC 1.5-3.6 mM) were chosen as micelle-forming surfactants and five dansylated hydrophobic amino acids were used as test analytes. The analytes were mutually separated by these micelles exhibiting almost similar migration times independent of the used surfactant. Baseline separations of all enantiomers were achieved using both beta-D-glucose and beta-D-galactose derivates that have an equatorially oriented hydroxy group at C-2 position. In contrast, the ability of enantioseparation was markedly decreased in the case of beta-D-mannose and 2-deoxy-beta-D-glucose derivatives. These results suggested that the structure of C-2 position of the sugar unit, namely presence of an equatorially oriented hydroxy group, is highly important for the enantiomeric separation of the chosen hydrophobic dansylated amino acids.
authors.affiliation: Graduate School of Environmental Science, Hokkaido University, Kita-ku, Hokkaido, Japan.
authors.forename: Chiharu
authors.initials: C
authors.lastname: Tano
authors.forename: Sang-Hyun
authors.initials: SH
authors.lastname: Son
authors.forename: Jun-Ichi
authors.initials: J
authors.lastname: Furukawa
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Furuike
authors.forename: Nobuo
authors.initials: N
authors.lastname: Sakairi
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification*; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D008823:Micelles; D010713:Phosphatidylcholines / Q000737:chemistry*; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: C496906:1-myristoyl-2-(12-((5-dimethylamino-1-naphthalenesulfonyl)amino)dodecanoyl)-sn-glycero-3-phosphocholine; D000596:Amino Acids; D008823:Micelles; D010713:Phosphatidylcholines; D013501:Surface-Active Agents; D013865:Thioglycosides; D005947:Glucose; D005690:Galactose