DRASTIC SOLVENT EFFECT ON LIPASE-CATALYZED ENANTIOSELECTIVE HYDROLYSIS OF PROCHIRAL 1,4-DIHYDROPYRIDINES

被引:103
作者
HIROSE, Y [1 ]
KARIYA, K [1 ]
SASAKI, I [1 ]
KURONO, Y [1 ]
EBIIKE, H [1 ]
ACHIWA, K [1 ]
机构
[1] UNIV SHIZUOKA,SCH PHARMACEUT SCI,SHIZUOKA 422,JAPAN
关键词
D O I
10.1016/S0040-4039(00)60861-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two enantiomers of 1,4-dihydropyridine compounds have been obtained with high enantiomeric purity by lipase-catalyzed hydrolysis in organic solvent saturated with water. Enantioselectivity of this reaction is dependent on the solvent used.
引用
收藏
页码:7157 / 7160
页数:4
相关论文
共 20 条
[1]  
BOLAND W, 1991, SYNTHESIS-STUTTGART, P1049
[2]   GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].
CHEN, CS ;
SIH, CJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707
[3]   ENZYMATIC CATALYSIS IN MONOPHASIC ORGANIC-SOLVENTS [J].
DORDICK, JS .
ENZYME AND MICROBIAL TECHNOLOGY, 1989, 11 (04) :194-211
[4]  
EBIIKE H, 1992, CHEM PHARM BULL, V40, P1083
[5]   ACYLOXYMETHYL AS AN ACTIVATING GROUP IN LIPASE-CATALYZED ENANTIOSELECTIVE HYDROLYSIS - A VERSATILE APPROACH TO CHIRAL 4-ARYL-1,4-DIHYDRO-2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATES [J].
EBIIKE, H ;
TERAO, Y ;
ACHIWA, K .
TETRAHEDRON LETTERS, 1991, 32 (41) :5805-5808
[6]   HOW CAN THE SOLVENT AFFECT ENZYME ENANTIOSELECTIVITY [J].
FITZPATRICK, PA ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :3166-3171
[7]   1,4-DIHYDROPYRIDINES - EFFECTS OF CHIRALITY AND CONFORMATION ON THE CALCIUM-ANTAGONIST AND CALCIUM AGONIST ACTIVITIES [J].
GOLDMANN, S ;
STOLTEFUSS, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1559-1578
[8]   A CHEMOENZYMATIC SYNTHESIS OF OPTICALLY-ACTIVE DIHYDROPYRIDINES [J].
HOLDGRUN, XK ;
SIH, CJ .
TETRAHEDRON LETTERS, 1991, 32 (29) :3465-3468
[9]   ENZYMES IN ORGANIC-SYNTHESIS [J].
JONES, JB .
TETRAHEDRON, 1986, 42 (13) :3351-3403
[10]   SOLVENT EFFECTS IN LIPASE-CATALYZED TRANSESTERIFICATION REACTIONS [J].
KANERVA, LT ;
VIHANTO, J ;
HALME, MH ;
LOPONEN, JM ;
EURANTO, EK .
ACTA CHEMICA SCANDINAVICA, 1990, 44 (10) :1032-1035