Preparation And Chiral Recognition Of Novel Cyclodextrin Derivatives Chiral Stationary Phases

It is well known that a pair of optically enantiomers often show quite difference inpharmacological and biological activities， especially in chiral drugs. Therefore， theenantioseparation is a continuously challenging task. Chromatography is one of the mosteffective methods for the enantioseparation. High performance liquid chromatography （HPLC）is fast， accurate and will not disrupt the structural and biological activity of enantiomers，which is widely used in agriculture， biology and so on. Thus， the research and developmenton the HPLC chiral stationary phases （CSPs） has always been the critical study. The chiralstationary phase was the most widely used in all of high performance liquid chromatographymeans. The cyclodextrin derivatives chiral stationary phase is one of the most widely studiedchiral stationary phases.In this thesis，5coated and5“click” bonded β-cyclodextrin derivative-based chiralstationary phases were prepared. The coated chiral stationary phases were prepared by coatedthe prepared phenylcarbamate β-cyclodextrin on aminopropyl silica gel. And the bondedchiral stationary phases were prepared by click reaction using6^A-N₃phenylcarbamateβ-cyclodextrin derivatives and alkynyl modified silica gel. The structures of the intermediatecompounds and products were characterized by infrared spectroscopy （IR），thermogravimetric analysis （TGA） and nuclear magnetic resonance spectroscopy （NMR）.The chiral reccgnition abilities of the obtained β-cyclodextrin derivative CSPs wereevaluated by HPLC. The results of tests indicated that the enantioseparation of the coatedphenylcarbamate β-CD CSP is better than that of the bonded CSP. The separation factor ofrac-4and rac-6with the coated phenylcarbamate β-CD CSP are1.08and1.58（H/I=90/10，v/v）. However the enantioseparation of the bonded substituted phenylcarbamate β-CD CSPsare better than that of the coated CSP. The separation factor of rac-4，rac-5and rac-9with thebonded4-chlorophenylcarbamate β-CD CSP are1.12（H/I=99/1， v/v），1.06（H/I=99/1， v/v）and1.04（H/I=50/50， v/v）， respectively. The separation factor of rac-4and rac-6with thebonded3,5-dichlorophenylcarbamate β-CD CSP are1.03and1.39（H/I=90/10，v/v）. Theseparation factor of rac-6with the bonded4-methyl phenylcarbamate β-CD CSP is1.09（H/I=90/10， v/v）. The enantioseparation of the coated and bonded3,5-dimethylphenylcarbamate β-CD CSP are much the same. The separation factor of rac-6 with the coated and bonded3,5-dimethylphenylcarbamate β-CD CSP are1.35and1.05（H/I=95/5， v/v）.