title: Simultaneous enantioseparation of monosaccharides derivatized with L-tryptophan by reversed phase HPLC.
abstract: Three reducing monosaccharides (glucose; Glc, galactose; Gal, and mannose; Man) were derivatized with L-tryptophan (L-Trp) under alkaline conditions. The DL-Gal and DL-Man derivatives were chirally resolved by HPLC with an acidic mobile phase, but the DL-Glc derivative was not. All of the three DL-monosaccharide derivatives were simultaneously enantioseparated using HPLC with a SunShell RP-AQUA column (C28) and a basic mobile phase. The optimum mobile phase conditions consisted of 5 mM phosphate and 25 mM tetraborate buffer (pH 9.6) at 20°C. With this system, resolution of D- and L-isomers of the Glc, Gal and Man derivatives were approximately 1.7, 2.2 and 2.4, respectively. When the three monosaccarides were derivatized with L-phenylalanine instead of L-Trp, DL-Gal and DL-Man were enantioseparated under both acidic and basic conditions, but DL-Glc was not. It was observed that enantiomer elution orders of the three monosaccharides derivatized with L-Trp were reasonably reversed when derivatized with D-Trp. It was also revealed that borate anions were required for simultaneous enantioseparation with HPLC.
authors.affiliation: School of Science, Tokai University.
authors.forename: Mami
authors.initials: M
authors.lastname: Akabane
authors.forename: Atsushi
authors.initials: A
authors.lastname: Yamamoto
authors.forename: Sen-ichi
authors.initials: S
authors.lastname: Aizawa
authors.forename: Atsushi
authors.initials: A
authors.lastname: Taga
authors.forename: Shuji
authors.initials: S
authors.lastname: Kodama
mesh_terms: D001880:Boranes / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005690:Galactose / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008358:Mannose / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D001880:Boranes; D009005:Monosaccharides; D014364:Tryptophan; D008358:Mannose; D005690:Galactose