title: Simultaneous Enantioseparation of Aldohexoses and Aldopentoses Derivatized With L-Tryptophanamide by Reversed Phase HPLC Using Butylboronic Acid as a Complexation Reagent of Monosaccharides.
abstract: Three aldohexoses, glucose, galactose, and mannose, and three aldopentoses, arabinose, xylose, and ribose, were derivatized with L-tryptophanamide (L-TrpNH2 ) under alkaline conditions. Using a basic mobile phase (pH 9.2), the three aldohexoses or the three aldopentoses were simultaneously enantioseparated, respectively, but all the six monosaccharides could not be simultaneously enantioseparated. A large amount of nonreacted L-TrpNH2 was detected after the derivatized monosaccharides. In order to widen the separation window, a large portion of nonreacted L-TrpNH2 could be eliminated by liquid-liquid extraction with ethylacetate, and elution order of the derivatized monosaccharides and nonreacted L-TrpNH2 was found to be reversed using a neutral mobile phase. All of the six monosaccharides were simultaneously enantioseparated by reversed phase high-performance liquid chromatography (HPLC) using InertSustainSwift C18 column (4.6 mm i.d. × 150 mm) and a mobile phase containing 180 mM phosphate buffer (pH 7.6), 1.5 mM butylboronic acid, and 5% acetonitrile at 40 °C. Nomenclature of D and L for monosaccharides is based on the configurations of the asymmetric C4 center for aldopentoses and C5 center for aldohexoses. It was found that the enantiomer elution order of these six monosaccharides and fucose in the proposed method conformed to be the absolute configuration of the C2 center.
authors.affiliation: School of Science, Tokai University, Kanagawa, Japan.
authors.forename: Mirei
authors.initials: M
authors.lastname: Shou
authors.affiliation: GL Sciences Inc., Tokyo, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Terashima
authors.affiliation: Graduate School of Science and Engineering, University of Toyama, Toyama, Japan.
authors.forename: Sen-Ichi
authors.initials: S
authors.lastname: Aizawa
authors.affiliation: Faculty of Pharmacy, Kinki University, Higashi-Osaka, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Taga
authors.affiliation: Department of Biological Chemistry, College of Bioscience and Biotechnology, Chubu University, Aichi, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Yamamoto
authors.affiliation: School of Science, Tokai University, Kanagawa, Japan.
authors.forename: Shuji
authors.initials: S
authors.lastname: Kodama
mesh_terms: D001089:Arabinose / Q000302:isolation & purification; D001896:Boron Compounds / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D056148:Chromatography, Reverse-Phase / Q000379:methods*; D005690:Galactose / Q000302:isolation & purification; D005947:Glucose / Q000302:isolation & purification; D006863:Hydrogen-Ion Concentration; D059625:Liquid-Liquid Extraction; D009005:Monosaccharides / Q000737:chemistry / Q000302:isolation & purification*; D012266:Ribose / Q000302:isolation & purification; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry; D014994:Xylose / Q000302:isolation & purification
chemical_list: D001896:Boron Compounds; D009005:Monosaccharides; C019585:tryptophanamide; C030433:n-butylboronic acid; D012266:Ribose; D014364:Tryptophan; D014994:Xylose; D001089:Arabinose; D005947:Glucose; D005690:Galactose
keywords: HPLC; butylboronic acid; enantioseparation; monosaccharide; tryptophanamide