Preparation And Application Of Cinchona Alkaloids Chiral Monolithic Column

Amino acids are the basic unit of the proteins,many amino acids have important physiological functions in the human body.Amino acid enantiomers have the same physical and chemical properties in the achiral environment,but the organism is a chiral environment,and the amino acids of different configurations are significantly different in biological and toxicological activities in the organism.Therefore,the chiral separation of amino acids is of great significance to the research of life science.Organic polymer chiral monolithic column has the advantages of simple preparation method,good permeability,high column capacity and good stability.It has shown advantages in the chiral recognition ability and efficiency of enantiomers of amino acid derivatives,which can effectively improve the traditional separation of chromatographic separation medium and have attracted much attention.Therefore,the research of this thesis revolves around the preparation and application of the highly selective organic polymer monolithic column.Part one,a quinine derivative O-9-(tert-butylcarbamoyl)-11-[(2-methacryloyloxy)ethylthio]-10,11-dihydroquinine(MBQN)was synthesized and used as a chiral monomer to prepared a poly(MBQN-co-HEMA-co-EDMA)chiral column by in-situ thermal polymerization.The composition,morphology and pore size distribution of monolithic column stationary phase were tested by scanning electron microscopy,elemental analysis and mercury porosimetry.In the microfluidic liquid chromatography mode,poly(MBQN-co-HEMA-co-EDMA)was used as the separation column to optimize the mobile phase,and 15 amino acid derivatives were separated.The results show that the monolithic column has good separation performance and excellent reproducibility.The second part,O-9-(tert-butylcarbamoyl)-11-[(2-methacryloyloxy)ethylthio]-10,11-dihydrocinchonine(MBCN)was prepared and purified by a three-step derivatization reaction.Using MBCN as chiral monomer,hydroxyethyl methacrylate(HEMA)as achiral monomer,ethylene glycol dimethacrylate(EDMA)as crosslinker,cyclohexanol and 1-dodecanol as two element pore system,two different poly(MBCNco-HEMA-co-EDMA)chiral monolithic columns were prepared by adjusting the proportion of chiral monomers in the polymer solution.The composition and morphology of two kinds of monolithic column stationary phases were tested by scanning electron microscopy and elemental analysis.Poly(MBCN-co-HEMA-coEDMA)Column 1 and poly(MBCN-co-HEMA-co-EDMA)Column 2 were used as separation columns to optimize the mobile phase for the separation of different amino acid derivatives.The experimental results show that the cinchonine monolithic column has good chiral separation performance and good reproducibility.The third part,O-9-(tert-butylcarbamoyl)-11-[(2-methacryloyloxy)ethylthio]-10,11-dihydrochonidine(MBCD)was prepared and purified by a three-step derivatization reaction.Using MBCD as chiral monomer,HEMA as achiral monomer,EDMA as crosslinker,cyclohexanol and 1-dodecanol as two element pore system,two different poly(MBCD-co-HEMA-co-EDMA)chiral monolithic columns were prepared by in-situ thermal polymerization with adjusting the proportion of chiral monomers in the polymer solution.The composition and morphology of two kinds of monolithic column stationary phases were tested by scanning electron microscopy and elemental analysis.Poly(MBCD-co-HEMA-co-EDMA)Column 3 and poly(MBCDco-HEMA-co-EDMA)Column 4 were used as separation columns to optimize the mobile phase for the separation of different amino acid derivatives.The experimental results show that the chonidine monolithic column has good chiral separation performance and good reproducibility.