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Synthesis and Chiral Separation of β-amino Acids

Author: ChenFeng
Tutor: WanQianHong
School: Tianjin University
Course: Pharmaceutical Analysis
Keywords: β-amino acid Chiral separation Chiral ligand exchange chromatography Chiral crown ether chromatography
CLC: TQ464
Type: Master's thesis
Year: 2007
Downloads: 386
Quote: 0
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Abstract


β-amino acid although less exist in nature , but its own , and compounds formed by it has shown a good pharmacological and biological activity . β-amino acids of the two enantiomers of different pharmacological effects in vivo , so try to get a single β-amino acid enantiomer is very important . Enantiomeric separation with the preparation of modern chromatographic separation techniques due to the fast , easy operation, and low cost and widespread attention , including chiral stationary phase chromatography of amino acids have been used to split , chiral crown ether phase chromatography ligand exchange stationary phase chromatography is the application of the better of the two . First article the racemic form of the six kinds of β-amino acid synthesized in a simple one-pot , five kinds of β-amino acid containing a benzene ring , a thiophene- β-amino acid . Synthesis process on the purification method has been improved to some extent, improved the yield . Then this paper commodity ligand exchange column be split, and the splitting process in the chromatography conditions were optimized , the effects of the concentration of copper ions in the mobile phase center , the content of the mobile phase, methanol , flow rate and pH the influence of the chiral separation , the separation factor obtained in the 1.14 to 2.70 . Ligand exchange chromatography in the preparation is necessary to remove the copper ions, which makes the preparation becomes difficult . We therefore simple D-tartaric acid as the raw material through a four-step reaction of the ( -) - (18 - crown-6) -2,3,11,12 - tetracarboxylic acid and its bonding on silica prepared chiral crown ether stationary phase . Chiral crown ethers chromatography split the synthesis of β-amino acid , wherein the separation factor of the three kinds of 1.16,1.20,1.20 . Β-amino acids by the synthesis and chiral separation , we expect to build a simple and quick method for the β-amino acid used in drug screening the preparation of the single enantiomers .

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