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Synthesis and Resolution Property of N-(9-Fluorenylmethoxycarbonyl)-D-Tryptophan and D-Phenylalanine Imprinted Polymer

Author: WangZhenXing
Tutor: DongHongXing
School: Harbin Engineering University
Course: Chemical Engineering
Keywords: molecular imprinted polymers high performance liquid chromatography frontal chromatography chiral separation adsorbance
CLC: O631.3
Type: Master's thesis
Year: 2011
Downloads: 13
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Abstract


N-(9-Fluorenylmethoxyca-rbonyl)-D-tryptophan imprinted polymers were prepared by thermal initiated polymerization and photo initiate polymerization. In order to obtain the best condition, the polymerization is firstly carried on the study of the functional monomer, crosslinker, initiator and reaction conditions on the preparation and performance of MIPs by the single factor. Then the polymers were evaluated by high performance liquid chromatography. The optimal conditions:acetonitrile was used as porogen, acrylamide as functional monomer, acetonitrile -acetic acid (98:2 V:V) as mobile phase, the flow rate as 0.1 mL/min, the column temperature as 25℃, the sample concentration as 0.2 mg/mL. For thermal initiated polymerization, N-(9-Fluorenylmethoxyca-rbonyl)-D, L-tryptophan can be well separated. The separate factor was 2.24. For photo initiated polymerization, N-(9-Fluorenylmethoxyca-rbonyl)-D, L-tryptophan can be well separated. The separate factor was 3.86. Besides, three amino acid derivatives racemates were well separated by the polymers. The separation factors were 1.74,1.66, and 1.21 for N-(9-Fluorenylmethoxycarb-onyl)-DL-phenylalanine,N-(phenylmethoxy)carbonyl-DL-trypto-phan and N-(phenylmethoxy)carbonyl-DL-phenylalanine respectively. By frontal chromatography, the results suggested that the dissociation constant for N-(9-Fluorenylmethoxyca-rbonyl)-D-tryptophan was 0.009 mol/L and the dissociation constant for N-(9-Fluorenylmethoxyca-rbonyl)-L-tryptophan was 0.03 mol/L.Then molecularly imprinted polymer in the aqueous suspension system was studied, D-Phenylalanine imprinted polymers were prepared by a novel method modified suspension polymerization. In order to obtain the best condition, the polymerization was firstly carried on the study of the functional monomer, crosslinker, initiator and reaction conditions on the preparation and performance of D-Phenylalanine imprinted polymers by the single factor and orthogonal experiment. Its optimal reaction conditions:Mixing speed was 300 r/min, the ratio of amount substance D-Phenylalanine, methacrylic acid, ethylene glycol dimethacrylate was 1:6:20, the amount of azodiisobutyronitrile was 0.6 g,60℃water bathing. By this, D-Phenylalanine imprinted polymer microspheres (MIMs) polymerization in relatively small average size (20μm) can be produced. In addition, the adsorption property of the polymers was evaluated. The saturated extent of adsorption was 0.53 mg/g,0.51mg/g and 0.21 mg/g for D-Phenylalanine, L-Phenylalanine and D-Tryptophane respectively. Then the polymers were evaluated by high performance liquid chromatography. When water as mobile phase and the flow rate was 0.1 ml/min, the separate factor was 1.05 for D, L-Phenylalanine and 2.61 for the compound of D-Phenylalanine and D- Tryptophane.

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CLC: > Mathematical sciences and chemical > Chemistry > Polymer chemistry ( polymer ) > Polymer physics and physical chemistry of polymers > The chemical nature of polymers
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