Study On The Chiral Recognition Mechanism Of Binaphthol On A Coatedamylose-derived Chiral Stationary Phase

In recent years, separation of enantiomers by high-performance liquidchromatography has been a very attractive domain. It almost involves all the frontierfields of life science. Though significant progress of enantioseparation by HPLC hasbeen achieved in the past, the corresponding mechanism study of chiral recognition islimited. While, as is known to all, the mechanism study of enantioseparation is ofgreat importance. It is useful to enable the chromatographer to design more effectivechiral stationary phases, to select better chromatographic conditions, and to developnovel chiral drugs.This paper mainly includes the following four aspects.1. The importance of enantioseparation by high-performance liquidchromatography is discussed in the Introduction section. The progress of the study onthe chiral recognition mechanism was also discussed. This part also gives a briefintroduction to the separation methods of chiral compounds.2. Several compounds including binaphthol (BINOL), binaphthol diacetate andhydrobenzion were enantioseparated on Amylose-2column under the normal phasecondition. Solvent-induced and temperature-induced reversal of elution order wereobserved in this case. When1-propanol and1-butanol were used, an uncommonphenomenon was observed. The retention time of R-BINOL increased with increaseof the column temperature, suggesting that it was the rare endothermic retentionprocess.3. Several compounds including flavanone,1-naphthylethanol, binaphtholdicinnamate, binaphthol disulfonate, benzoin, binaphthol diacetate, and warfarin wereenantioseparated on Amylose-2column in the organic solvent mode. Flavanone,binaphthol dicinnamate, benzoin, and warfarin achieved satisfatory separation, butbinaphthol disulfonate can not. The linear range for warfarin was0.005~4mg/mL.4. Enantioseparation of BINOL, BINOL dicinnamate and naproxen on a tartaricacid-derived CSP, Kromasil-DMB, was investigated in the normal phase mode. Theeffects of column temperature and polar alcohol modifier in the mobile phase on theretention, enantioseparation and elution order were investigated. Baseline enantioseparation could be achieved for binaphthol and binaphthol dicinnamate,naproxen achieved a partial enantioseparation.