title: Separation of derivatized glucoside anomers using supercritical fluid chromatography.
abstract: Preparative scale supercritical fluid chromatography was used to separate derivatized anomeric monosaccharides. Methyl 2,3,4,6-tetra-O-benzoyl-α-d-glucopyranoside and methyl 2,3,4,6-tetra-O-benzoyl-β-d-glucopyranoside were synthesized by benzoyl derivatization of the parent anomerically pure monosaccharides. The elution profiles of each anomer were studied, suggesting that separation was possible. Mixtures of the compounds were then prepared at different ratios and separation was achieved using carbon dioxide/ethanol mixtures as the mobile phase and GreenSep™ 5micron particle size silica as the stationary phase. Ethanol co-solvent in the mobile phase was required to give a successful separation of the anomers however over the range 6.5-10.4wt% ethanol concentration studied here there was little variation in the degree of separation. In fractionation trials, separation of mixtures into fractions with >98% purity was achieved, with recoveries greater than 96%.
authors.affiliation: Integrated Bioactive Technologies, Callaghan Innovation, 69 Gracefield Road, 5040 Lower Hutt, New Zealand. Electronic address: Fernando.Montanes@callaghaninnovation.govt.nz.
authors.forename: Fernando
authors.initials: F
authors.lastname: Montañés
authors.affiliation: Integrated Bioactive Technologies, Callaghan Innovation, 69 Gracefield Road, 5040 Lower Hutt, New Zealand.
authors.forename: Paul
authors.initials: P
authors.lastname: Rose
authors.affiliation: Integrated Bioactive Technologies, Callaghan Innovation, 69 Gracefield Road, 5040 Lower Hutt, New Zealand.
authors.forename: Stephen
authors.initials: S
authors.lastname: Tallon
authors.affiliation: Integrated Bioactive Technologies, Callaghan Innovation, 69 Gracefield Road, 5040 Lower Hutt, New Zealand.
authors.forename: Rahau
authors.initials: R
authors.lastname: Shirazi
mesh_terms: D002245:Carbon Dioxide; D025924:Chromatography, Supercritical Fluid / Q000379:methods; D003487:Cyanoacrylates; D004659:Enbucrilate; D000431:Ethanol; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification*; D012822:Silicon Dioxide; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D003487:Cyanoacrylates; D005960:Glucosides; D012997:Solvents; C000606009:methyl 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranoside; D002245:Carbon Dioxide; D000431:Ethanol; D012822:Silicon Dioxide; D004659:Enbucrilate
keywords: Carbohydrates; Chromatography; Supercritical; UV detection