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The Preparation of Coupling Oligo-β-Cyclodextrin on Polyvinyl-Acetate Medium and Its Application for Screening Bioactive Natural Products

Author: LiZuo
Tutor: TanTianWei
School: Beijing University of Chemical Technology
Course: Chemical Engineering and Technology
Keywords: β-cyclodextrin Polyethylene vinyl acetate resin Puerarin Separation and purification
CLC: TQ325
Type: Master's thesis
Year: 2010
Downloads: 78
Quote: 0
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Abstract


the hydrophilic nature of the β-cyclodextrin hydrophobic outer as well as the special molecular structure, it has the ability to identify and select the guest molecules by virtue of differences in size, geometry and nature. Advantage of this ability to form inclusion complexes with particular guest molecules, the β-cyclodextrin may be bonded to a suitable carrier, for the preparative liquid chromatography stationary phase, and to improve the separation ability of the medium. Β-cyclodextrin bonded to a polyethylene vinyl acetate polymer adsorption resin, to improve the separation efficiency of the active ingredient in its natural product, to overcome the natural polysaccharides of the β-cyclodextrin bonded gel medium mechanical strength is not high the shortcomings can not tolerate certain organic solvents, new chromatographic separation media, the active ingredients of natural products for the separation and purification of puerarin plant achieved good separation effects. Optimize the preparation of β-cyclodextrin polymer activation and bonding conditions, adsorption to retain of puerarin the mechanism discussed them. Including the following three parts: the first part is the synthesis and characterization of the medium. By suspension polymerization independent synthetic resin P (VAC-TAIC-DVB)-β-cyclodextrin, morphology and pore structure on the surface of the medium, characterized by scanning electron microscopy, infrared spectroscopy and pressure mercury analyzer; by alcoholysis reaction and the ring reaction with oxygen so that by the two-step activation before the resin in the grafted cyclodextrin has a larger content of an epoxy group, the optimal conditions for the alcoholysis reaction: Alkalinity 3%, activation 15H, hydroxyl content of up to 22mmol / g, an epoxy optimal conditions of reaction feeding mode for adding lye before adding epichlorohydrin, an epoxy group content of 40μmol / g; determined P (VAC-TAIC-DVB) resin-bonded β-cyclodextrin: bonded solvent system is DMF / NaCl solution, the bonding time 20H, temperature 70 ℃, the quality of the feed ratio of 1:2 under the reaction conditions (resin / β-CD), the amount of immobilized β-CD to 10μmol / g. The second part is the application of the the bonding media in the chromatographic separation. P (VAC-TAIC-DVB)-β-CD the chromatography medium separation puerarin, daidzin and daidzein mixture mobile phase consisting of methanol / 7% HAc solution. Puerarin and daidzein can be separated under the conditions of the methanol concentration of 40%, purity more than 98%, yield 80% under the conditions of the methanol concentration in the range of 40-50%;, daidzin and daidzein can to be separated; three substances can be separated using a gradient elution of methanol and 7% HAc solution, degree of separation up to 0.894 and 2.787, purity range of 55-90%, and the yield of about 30-40%. The third part, the authors combined the adsorption kinetics and molecular dynamics simulation of experimental phenomena Mechanism. Microspheres, polyvinyl acetate the static adsorption meets puerarin Freundlich model, add a cross-linking agent TAIC resin bonding Gibbs free energy of β-cyclodextrin, the system can be increased, so that the adsorption amount increases; discovered by molecular dynamics simulations, the TAIC six-membered ring with puerarin C ring combination, and TAIC carbonyl puerarin on glucose units the hydroxyl formation of hydrogen bonds, the DVB on the benzene ring with puerarin A ring binding, no hydrogen bonding interactions; through the adsorption performance was measured in static experiments after sodium dodecyl sulfate, and urea is added, the adsorption process is the joint action of the role of hydrogen bonding and hydrophobic; retention time with temperature through the investigated column separation changes confirmed the hydrogen bonding interaction is indeed exist.

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