Kinetic resolution of propranolol by a lipase-catalyzed N-acetylation

被引:45
作者
Chiou, TW
Chang, CC
Lai, CT
Tai, DF
机构
[1] ACAD SINICA,INST CHEM,TAIPEI,TAIWAN
[2] DA YEH INST TECHNOL,CTR BIOCHEM ENGN,CHANGHUA,TAIWAN
[3] NATL DONG HWA UNIV,DEPT CHEM,HUALIEN,TAIWAN
关键词
D O I
10.1016/S0960-894X(97)00028-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An enzymatic method for the direct resolution of propranolol is described. Candida cylindracea lipase enantioselectively catalyzed N-acetylation of S-propranolol with isopropenyl acetate in isopropyl ether, The ee values of the two enantiomers of N-acetylpropranolol were determined by an HPLC equipped with a chiral column. The effects of organic solvent nature and substrate concentration on enantioselectivity were also studied. (C) 1997, Elsevier Science Ltd.
引用
收藏
页码:433 / 436
页数:4
相关论文
共 29 条
[1]   PRACTICAL CHEMOENZYMATIC SYNTHESIS OF BOTH ENANTIOMERS OF PROPRANOLOL [J].
BEVINAKATTI, HS ;
BANERJI, AA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5372-5375
[2]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[3]   THE CLINICAL IMPORTANCE OF CARDIOSELECTIVITY AND LIPOPHILICITY IN BETA-BLOCKERS [J].
CRUICKSHANK, JM .
AMERICAN HEART JOURNAL, 1980, 100 (02) :160-178
[4]  
FRISHMAN WH, 1982, NEW ENGL J MED, V306, P1456
[5]   AN ENZYMATIC METHOD FOR THE PREPARATION OF CHIRAL DIAMIDES [J].
GOTOR, V ;
GARCIA, MJ ;
REBOLLEDO, F .
TETRAHEDRON-ASYMMETRY, 1990, 1 (05) :277-278
[6]  
GOTOR V, 1991, TETRAHEDRON, V47, P9209
[7]   CHIRAL SEPARATION OF PROPRANOLOL AND ITS ESTER DERIVATIVES ON AN OVOMUCOID-BONDED SILICA - INFLUENCE OF PH, IONIC-STRENGTH AND ORGANIC MODIFIER ON RETENTION, ENANTIOSELECTIVITY AND ENANTIOMERIC ELUTION ORDER [J].
HAGINAKA, J ;
WAKAI, J ;
TAKAHASHI, K ;
YASUDA, H ;
KATAGI, T .
CHROMATOGRAPHIA, 1990, 29 (11-12) :587-592
[8]   RESOLUTION OF RACEMIC AMINOALCOHOLS (BETA-BLOCKERS), AMINES AND ACIDS AS ENANTIOMERIC DERIVATIVES USING A CHIRAL ALPHA-1-ACID GLYCOPROTEIN COLUMN [J].
HERMANSSON, J .
JOURNAL OF CHROMATOGRAPHY, 1985, 325 (02) :379-384
[9]  
HOLTZMAN JL, 1982, J CHROMATOGR, V238, P470
[10]   LIPASE-CATALYZED RESOLUTION - ENANTIOSELECTIVE ESTERIFICATION OF 2-PROPANOL AMINES [J].
KAMAL, A ;
RAO, MV .
TETRAHEDRON-ASYMMETRY, 1991, 2 (08) :751-754