Separation of derivatized glucoside anomers using supercritical fluid chromatography. 2015

Fernando Montañés, and Paul Rose, and Stephen Tallon, and Rahau Shirazi
Integrated Bioactive Technologies, Callaghan Innovation, 69 Gracefield Road, 5040 Lower Hutt, New Zealand. Electronic address: Fernando.Montanes@callaghaninnovation.govt.nz.

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%.

UI MeSH Term Description Entries
D002245 Carbon Dioxide A colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbonic Anhydride,Anhydride, Carbonic,Dioxide, Carbon
D003487 Cyanoacrylates A group of compounds having the general formula CH2 Cyanoacrylate
D004659 Enbucrilate A tissue adhesive that is applied as a monomer to moist tissue and polymerizes to form a bond. It is slowly biodegradable and used in all kinds of surgery, including dental. Butylcyanoacrylate,2-Cyanobutylacrylate,Butyl 2-Cyanacrylate,Chirurcoll,Enbucrilate, Homopolymer,Enbucrylate,Fimomed,Histacryl,Histoacryl,Histoacryl Blue,Histoacryl N-blau,Kanokonlit,Ligament-Fimomed,N-Butyl-2-Cyanoacrylate,N-Butyl-Cyanoacrylate,NBCA compound,Poly(Isobutyl Cyanoacrylate),Polybutyl Cyanoacrylate,Polyisobutyl Cyanoacrylate,Polyisobutylcyanoacrylate,2 Cyanobutylacrylate,2-Cyanobutylacrylates,Butyl 2 Cyanacrylate,Butyl 2-Cyanacrylates,Butylcyanoacrylates,Cyanoacrylate, Polybutyl,Cyanoacrylate, Polyisobutyl,Cyanoacrylates, Polybutyl,Cyanoacrylates, Polyisobutyl,Enbucrilates,Enbucrilates, Homopolymer,Enbucrylates,Histacryls,Histoacryl N blau,Histoacryls,N Butyl 2 Cyanoacrylate,N Butyl Cyanoacrylate,N-Butyl-2-Cyanoacrylates,N-Butyl-Cyanoacrylates,NBCA compounds,Polybutyl Cyanoacrylates,Polyisobutyl Cyanoacrylates,Polyisobutylcyanoacrylates
D005960 Glucosides A GLYCOSIDE that is derived from GLUCOSE. Glucoside
D000431 Ethanol A clear, colorless liquid rapidly absorbed from the gastrointestinal tract and distributed throughout the body. It has bactericidal activity and is used often as a topical disinfectant. It is widely used as a solvent and preservative in pharmaceutical preparations as well as serving as the primary ingredient in ALCOHOLIC BEVERAGES. Alcohol, Ethyl,Absolute Alcohol,Grain Alcohol,Alcohol, Absolute,Alcohol, Grain,Ethyl Alcohol
D012822 Silicon Dioxide Transparent, tasteless crystals found in nature as agate, amethyst, chalcedony, cristobalite, flint, sand, QUARTZ, and tridymite. The compound is insoluble in water or acids except hydrofluoric acid. Silica,Aerosil,Aerosil 380,Cristobalite,Quso G-32,Quso G32,Tridymite,380, Aerosil,Dioxide, Silicon,G32, Quso,Quso G 32
D012997 Solvents Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant & Hackh's Chemical Dictionary, 5th ed) Solvent
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D025924 Chromatography, Supercritical Fluid A CHROMATOGRAPHY method using supercritical fluid, usually carbon dioxide under very high pressure (around 73 atmospheres or 1070 psi at room temperature) as the mobile phase. Other solvents are sometimes added as modifiers. This is used both for analytical (SFC) and extraction (SFE) purposes. Supercritical Fluid Chromatography,Supercritical Fluid Extraction,Extraction, Supercritical Fluid,SFC (Supercritical Fluid Chromatography),SFE (Supercritical Fluid Extraction),Fluid Chromatography, Supercritical,Fluid Extraction, Supercritical

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