title: Chiral separation of D/L-aldoses by micellar electrokinetic chromatography using a chiral derivatization reagent and a phenylboronic acid complex.
abstract: A novel method was developed for D/L-isomeric separation of aldopentoses and aldohexoses as their (S)-(+)-4-(N,N-dimethylaminosulfonyl)-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole derivatives using phenylboronate buffer containing sodium dodecyl sulfate as a background electrolyte. The combination of derivatization with a chiral labeling reagent and micellar electrokinetic chromatography with phenylboronate made possible the efficient separation of D/L isomers as well as epimeric isomers of aldopentoses and aldohexoses. Laser-induced fluorescence detection permitted the micromolar-level determination of monosaccharide derivatives. The limit of detection was 105 amol (300 nM), and the repeatabilities of the migration times and peak area responses were 0.8 % and 7.9 % (relative standard deviation; n = 6), respectively. The method was applied to the determination of D/L- galactose in red seaweed.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi, Osaka, 577-8502, Japan, yamamoto@phar.kindai.ac.jp.
authors.forename: Sachio
authors.initials: S
authors.lastname: Yamamoto
authors.forename: Yoko
authors.initials: Y
authors.lastname: Tamata
authors.forename: Kaori
authors.initials: K
authors.lastname: Sejima
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Kinoshita
authors.forename: Shigeo
authors.initials: S
authors.lastname: Suzuki
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods; D005690:Galactose / Q000032:analysis / Q000302:isolation & purification; D006601:Hexoses / Q000032:analysis / Q000302:isolation & purification*; D010069:Oxadiazoles / Q000032:analysis / Q000302:isolation & purification*; D010429:Pentoses / Q000032:analysis / Q000302:isolation & purification*; D012624:Seaweed / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000032:analysis / Q000302:isolation & purification*
chemical_list: C117768:4-(N,N-dimethylaminosulfonyl)-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole; D001897:Boronic Acids; D006601:Hexoses; D010069:Oxadiazoles; D010429:Pentoses; D013449:Sulfonamides; C010686:benzeneboronic acid; D005690:Galactose