SEPARATION OF SOME ENANTIOMERS AND DIASTEREOMERS OF PROPRANOLOL DERIVATIVES BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY

被引:23
作者
FACKLAM, C
MODLER, A
机构
[1] Max-Planck-Gesellschaft, Arbeitsgruppe Asymmetrische Katalyse an der Universitat Rostock (in the Inst. fur Organische Katalys, 18055 Rostock
关键词
D O I
10.1016/0021-9673(94)87009-8
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The separation of some propranolol analogues I into their enantiomers and diastereomers respectively, by HPLC succeeded with cellulose tris(3,5-dimethylphenylcarbamate) as a chiral stationary phase and hexane-alcohol and aqueous NaClO4-acetonitrile as mobile phases. Retention times and alpha values depend on the substituents R(1) and R(2). With non-aromatic substituents R(1) or R(2) the R-enantiomers are eluted first whereas with aromatic substituents the S-enantiomers, surprisingly, have shorter retention times. [GRAPHICS] ]
引用
收藏
页码:203 / 211
页数:9
相关论文
共 13 条
[1]   CHROMATOGRAPHIC RESOLUTION OF THE CHIRAL ISOMERS OF SEVERAL BETA-BLOCKERS OVER CELLULOSE TRIS(3,5-DIMETHYLPHENYLCARBAMATE) CHIRAL STATIONARY PHASE [J].
CHING, CB ;
LIM, BG ;
LEE, EJD ;
NG, SC .
CHIRALITY, 1992, 4 (03) :174-177
[2]   RETENTION, ENANTIOSELECTIVITY AND ENANTIOMERIC ELUTION ORDER OF PROPRANOLOL AND ITS ESTER DERIVATIVES ON AN ALPHA1-ACID GLYCOPROTEIN-BONDED COLUMN [J].
HAGINAKA, J ;
SEYAMA, C ;
YASUDA, H ;
TAKAHASHI, K .
CHROMATOGRAPHIA, 1992, 33 (3-4) :127-132
[3]   CELLULOSIC CHIRAL STATIONARY PHASE UNDER REVERSED-PHASE CONDITION [J].
ISHIKAWA, A ;
SHIBATA, T .
JOURNAL OF LIQUID CHROMATOGRAPHY, 1993, 16 (04) :859-878
[4]  
JIRA T, 1991, PHARMAZIE, V46, P432
[5]  
KRAUSE HW, 1992, PHARMAZIE, V47, P838
[6]   LIQUID AND HIGH-PRESSURE CARBON-DIOXIDE CHROMATOGRAPHY OF BETA-BLOCKERS - RESOLUTION OF THE ENANTIOMERS OF NADOLOL [J].
LEE, CR ;
PORZIEMSKY, JP ;
AUBERT, MC ;
KRSTULOVIC, AM .
JOURNAL OF CHROMATOGRAPHY, 1991, 539 (01) :55-69
[7]   CHROMATOGRAPHIC RESOLUTION .12. OPTICAL RESOLUTION OF BETA-BLOCKERS BY HPLC ON CELLULOSE TRIPHENYLCARBAMATE DERIVATIVES [J].
OKAMOTO, Y ;
KAWASHIMA, M ;
ABURATANI, R ;
HATADA, K ;
NISHIYAMA, T ;
MASUDA, M .
CHEMISTRY LETTERS, 1986, (07) :1237-1240
[8]   CHIRAL SEPARATIONS OF BETA-BLOCKING DRUG SUBSTANCES USING DERIVATIZATION WITH CHIRAL REAGENTS AND NORMAL-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
OLSEN, L ;
BRONNUMHANSEN, K ;
HELBOE, P ;
JORGENSEN, GH ;
KRYGER, S .
JOURNAL OF CHROMATOGRAPHY, 1993, 636 (02) :231-241
[9]   DIRECT ENANTIOMERIC SEPARATION OF BETA-BLOCKERS ON CHYROSINE-A BY SUPERCRITICAL FLUID CHROMATOGRAPHY - SUPERCRITICAL CARBON-DIOXIDE AS TRANSIENT INSITU DERIVATIZING AGENT [J].
SIRET, L ;
BARGMANN, N ;
TAMBUTE, A ;
CAUDE, M .
CHIRALITY, 1992, 4 (04) :252-262
[10]   IMPROVEMENT OF THE ENANTIORECOGNITION ABILITY OF TYROSINE-DERIVED CHIRAL STATIONARY PHASES - DIRECT RESOLUTION OF 1,2-AMINO-ALCOHOLS (BETA-BLOCKERS) [J].
TAMBUTE, A ;
SIRET, L ;
BEGOS, A ;
CAUDE, M .
CHIRALITY, 1992, 4 (01) :36-42