Stereochemical resolution of racemates, in HPLC, using a chiral stationary phase based upon immobilized α-chymotrypsin.: I.: Structural chiral separations

被引:40
作者
Félix, G [1 ]
Descorps, V [1 ]
机构
[1] ENSCPB, F-33402 Talence, France
关键词
column liquid chromatography; alpha-chymotrypsin immobilized on silica; in situ immobilization process; structural chiral separations;
D O I
10.1007/BF02466900
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
alpha-Chymotrypsin was immobilized on an epoxide derivatized silica gel by an in situ immobilization process. Several racemates were resolved by a structural recognition mechanism. The immobilization process and the stability of this alpha-chymotrypsin stationary phase have been studied. The mobile phase parameters including the ionic strength, pH and the effects of organic modifiers have been also investigated. The retention, efficiency and stereoselectivity of the solutes appear to be related to their molecular structure, hydrophobicity and electrostatic interactions. These relationships determine the recognition mechanism and the position of each enantiomer in the active site.
引用
收藏
页码:595 / 605
页数:11
相关论文
共 46 条
[11]  
DERNONCOUR R, 1984, THESIS U PARIS SUD
[12]  
Desnuelle P, 1960, ENZYMES
[13]  
DOMENCI E, 1990, J PHARM SCI, V80, P164
[14]   SYNTHESIS AND CHROMATOGRAPHIC PROPERTIES OF AN HPLC CHIRAL STATIONARY PHASE BASED UPON HUMAN SERUM-ALBUMIN [J].
DOMENICI, E ;
BERTUCCI, C ;
SALVADORI, P ;
FELIX, G ;
CAHAGNE, I ;
MOTELLIER, S ;
WAINER, IW .
CHROMATOGRAPHIA, 1990, 29 (3-4) :170-176
[15]   SPECIFICITY OF ALPHA-CHYMOTRYPSIN - SEPARATION OF POLAR, STERIC, AND SPECIFIC EFFECTS IN ALPHA-CHYMOTRYPSIN-CATALYZED HYDROLYSIS OF ACYL-SUBSTITUTED PARA-NITROPHENYL ESTERS [J].
DUPAIX, A ;
BECHET, JJ ;
ROUCOUS, C .
BIOCHEMISTRY, 1973, 12 (14) :2559-2566
[16]   IMMOBILIZED CELLULASE (CBH I) AS A CHIRAL STATIONARY PHASE FOR DIRECT RESOLUTION OF ENANTIOMERS [J].
ERLANDSSON, P ;
MARLE, I ;
HANSSON, L ;
ISAKSSON, R ;
PETTERSSON, C ;
PETTERSSON, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4573-4574
[17]  
FELIX G, 1989, BIOSCIENCE, V8, P2
[18]   LIQUID-CHROMATOGRAPHIC RESOLUTION OF RACEMIC DRUGS USING A CHIRAL ALPHA-1-ACID GLYCOPROTEIN COLUMN [J].
HERMANSSON, J .
JOURNAL OF CHROMATOGRAPHY, 1984, 298 (01) :67-78
[19]   DIRECT LIQUID-CHROMATOGRAPHIC RESOLUTION OF RACEMIC DRUGS USING ALPHA-1-ACID GLYCOPROTEIN AS THE CHIRAL STATIONARY PHASE [J].
HERMANSSON, J .
JOURNAL OF CHROMATOGRAPHY, 1983, 269 (02) :71-80
[20]   OPTIMIZATION OF THE SEPARATION OF ENANTIOMERS OF BASIC DRUGS - RETENTION MECHANISMS AND DYNAMIC MODIFICATION OF THE CHIRAL BONDING PROPERTIES ON AN ALPHA(1)-ACID GLYCOPROTEIN COLUMN [J].
HERMANSSON, J ;
GRAHN, A .
JOURNAL OF CHROMATOGRAPHY A, 1995, 694 (01) :57-69