CHIRAL STATIONARY PHASES CONSISTING OF AXIALLY DISSYMMETRIC 2'-SUBSTITUTED-1,1'-BINAPHTHYL-2-CARBOXYLIC ACIDS BONDED TO SILICA-GEL FOR HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS

被引：17

作者：

OI, S

SHIJO, M

TANAKA, H

MIYANO, S

YAMASHITA, J

机构：

[1] TOHOKU UNIV,FAC ENGN,DEPT BIOCHEM & ENGN,AOBA KU,SENDAI,MIYAGI 980,JAPAN

[2] TOKYO MED COLL,DEPT CHEM,SHINJUKU KU,TOKYO 160,JAPAN

来源：

JOURNAL OF CHROMATOGRAPHY | 1993年 / 645卷 / 01期

关键词：

D O I：

10.1016/0021-9673(93)80614-E

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

Seven chiral stationary phases (CSPs) were prepared by bonding axially dissymmetric 2'-substituted-1,1'-binaphthyl-2-carboxylic acids to aminoalkylsilanized silica gels through an amide linkage, and the effect of the 2'-substituents (CN, COOH, CONH2, CONHEt, CONEt2 and OCH3) was investigated for the high-performance liquid chromatographic (HPLC) separation of enantiomers. Among these CSPs, that which had a 2'-carboxyl substituent showed the best performance and efficiently discriminated several enantiomeric amino acids, amines and alcohols as their 3,5-dinitrophenyl derivatives, and biaryls bearing 2,2'-polar substituents, by normal-phase HPLC. Stereoselective pi-donor-acceptor interaction and dipole stacking interaction between the CSPs and the analytes seem to play a critical role in the enantioseparation.

引用

收藏

页码：17 / 28

页数：12

相关论文

共 30 条

[1] DIRECT RESOLUTION OF ENANTIOMERS BY LIQUID-CHROMATOGRAPHY WITH THE NOVEL CHIRAL STATIONARY PHASE DERIVED FROM (R,R)-TARTRAMIDE [J].

DOBASHI, Y ;

HARA, S .

TETRAHEDRON LETTERS, 1985, 26 (35) :4217-4220

[2]

HESSE G, 1976, LIEBIGS ANN CHEM, P966

[3] CHIRAL DIFFERENTIATION BY THE P-(+)-HEXAHELICENE-7,7'-DICARBOXYLIC ACID DISODIUM SALT - RESOLUTION OF N-2,4-DINITROPHENYL-ALPHA-AMINO-ACID ESTERS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

KIM, YH ;

BALAN, A ;

TISHBEE, A ;

GILAV, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (23) :1336-1337

[4] RESOLUTION OF OPTICAL ISOMERS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY, USING COATED AND BONDED CHIRAL CHARGE-TRANSFER COMPLEXING AGENTS AS STATIONARY PHASES [J].

MIKES, F ;

BOSHART, G ;

GILAV, E .

JOURNAL OF CHROMATOGRAPHY, 1976, 122 (JUL7) :205-221

[5] RESOLUTION OF OPTICAL ISOMERS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY - COMPARISON OF 2 SELECTOR-SELECTAND SYSTEMS [J].

MIKES, F ;

BOSHART, G .

JOURNAL OF CHROMATOGRAPHY, 1978, 149 (FEB) :455-464

[6] OPTICAL RESOLUTION OF 2'-METHOXY-1,1'-BINAPHTHYL-2-CARBOXYLIC ACID, AND APPLICATION TO CHIRAL DERIVATIZING AGENT FOR HPLC SEPARATION OF ENANTIOMERIC ALCOHOLS AND AMINES [J].

MIYANO, S ;

OKADA, S ;

HOTTA, H ;

TAKEDA, M ;

KABUTO, C ;

HASHIMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (05) :1528-1533

[7] PRACTICAL SYNTHESIS OF 1,1'-BINAPHTHYL-2-CARBOXYLIC ACIDS VIA SIDE-CHAIN OXIDATION OF 2-METHYL-1,1'-BINAPHTHYLS [J].

MIYANO, S ;

OKADA, S ;

SUZUKI, T ;

HANDA, S ;

HASHIMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (06) :2044-2046

[8] USE OF AXIALLY CHIRAL 2'-METHOXY-1,1'-BINAPHTHYL-2-CARBOXYLIC ACID AS CHIRAL DERIVATIZING AGENT FOR DISCRIMINATION OF ENANTIOMERIC ALCOHOLS AND AMINES BY (1-H)NMR [J].

MIYANO, S ;

OKADA, S ;

HOTTA, H ;

TAKEDA, MY ;

SUZUKI, TS ;

KABUTO, C ;

YASUHARA, FJ .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (12) :3886-3891

[9] ASYMMETRIC-SYNTHESIS OF AXIALLY CHIRAL, UNSYMMETRICAL DIPHENIC ACIDS VIA INTRAMOLECULAR ULLMANN COUPLING REACTION [J].

MIYANO, S ;

FUKUSHIMA, H ;

HANDA, S ;

ITO, H ;

HASHIMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (09) :3249-3254

[10] HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS ON (S)-2-(4-CHLOROPHENYL)ISOVALERIC ACID AND ITS AMIDE DERIVATIVES BONDED TO SILICA-GEL [J].

OI, N ;

NAGASE, M ;

INDA, Y ;

DOI, T .

JOURNAL OF CHROMATOGRAPHY, 1983, 265 (01) :111-116