Study On Binaphthol Derivative Used As Chiral Stationary Phase In HPLC

The optical resolution is a point of departure for chiral studies.In recent years,the enantioseparation has made remarkable progress,especially in chromatographic chiral stationary phases.In this work,the binaphthol enantiomer derivatives were investigated as liquid phase stationary phases.Three new CSPs R-(3,3?-halogen substituted-1,1'-binaphthyl)-20-crown-6(halogen = Cl,Br and I),namely R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6(CSP-1),R-(3,3'-dichloro-1,1'-binaphthyl)-20-crown-6(CSP-2)and R-(3,3'-diiodo-1,1'-binaphthyl)-20-crown-6(CSP-3)were prepared to test the effect of different CSP structures on the recognition of racemic amino acids.The experimental results indicated that all twenty-one ?-amino acids were different degrees of separation on CSP-1 at room temperature.20 ?-amino acids could be separated on CSP-2,however,CSP-3 only separated four amino acids,glutamine,asparagines,leucine and alanine.The R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6(CSP-1)possesses more prominent enantioselectivity than another two halogen-substituted crown ether derivatives.Both the separation factors(?)and the resolution values(Rs)on CSP-1 are better than that of commercial crown ether-based CSPs(CROWNPAK CR(+)from Daicel)under the same conditions for asparagine,threonine,proline,arginine,serine,histidine and valine,which cannot be separated by commercial CR(+).The(R)-(+)-1,1'-bi-2-naphthol was used to synthesize the(R)-3,3'-dipyridine-2,2'-dimethoxy-1,1'-binaphthyl derivatives and the(R)-3,3'-dibenzoic acid-2,2'-dimethoxy-1,1'-binaphthyl,some chiral enantiomers including 1,2-diphenylethylene oxide,warfarin,praziquantel,atenolol,metoprolol,amlodipine,DNB-leucine,phenylglycine,glutamic acid,leucine,threonine,and some aromatic positional isomers may be separated on their chiral columns by HPLC.