Synthesis Of Resin Loaded With Chiral Helical Foldamers And Their Application Of Chiral Separation

Because of their stable cavities,artificial helical foldamers have been extensively studied in the fields of molecular encapsulation,fluorescent probes,biomimetic channels,catalysis and changing the activity of biological macromolecules.In order to expand the application of helical foldamers in the field of chiral separation,this thesis prepared a series of resin loaded with chiral helixes,and the separation performance of enantiomers was studied through the different interactions among the compounds and the helical backbones as well as their cavities.First of all,the Merrifield resin was used as the starting material in this thesis,and the derivatives of resin were prepared by the solid phase peptide synthesis.According to the color of the ninhydrin indicator,the preparation of the desired resin was confirmed.Then the oligomers attached to the resin were cleaved by the method for aminolysis,and the chirality of the oligomers and the target resin was studied respectively.The results of ~1H Nuclear Magnetic Resonance(NMR)spectrum and Circular Dichroism(CD)spectrum showed that the oligomers connected to the R-chiral group formed M-helix,the oligomers connected to the S-chiral group formed P-helix,and the resin loaded with helical foldamers could still keep the helical chirality.Finally,this thesis evaluated the separation ability of the resin loaded with P-helixes for chiral compounds as the stationary phase,and used the blank resin and the resin loaded with the chiral dimer as control groups.Although having general separation effects on small chiral compounds,the resin loaded with chiral helixes had excellent separation performance on helical foldamers.The interactions of the resin loaded with M-helix on R-compounds were better than S-compounds.Neither the blank resin nor the resin loaded with the chiral dimer could separate the enantiomers.The research showed that resin loaded with chiral helixes relied on helical foldamers rather than chiral groups to separate enantiomers.