E/Z DIASTEROSELECTIVE ENZYMATIC-HYDROLYSIS OF ESTERS AND DIESTERS

被引:3
作者
SCHIRMEISTER, T [1 ]
OTTO, HH [1 ]
机构
[1] UNIV FREIBURG,INST PHARMAZEUT,LS PHARMAZEUT CHEM,HERMANN HERDER STR 9,W-7800 FREIBURG,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 04期
关键词
D O I
10.1002/anie.199305721
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
With porcine liver esterase the α,β‐unsaturated diester 1 can be hydrolyzed selectively at the ester group in the Z position relative to the carbonyl group. The further saponification to give the dicarboxylic acid is achieved with aqueous NaOH. However, even under drastic conditions, 1 cannot be hydrolyzed in one step by either bases or acids with retention of the β‐lactam ring. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany
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页码:572 / 574
页数:3
相关论文
共 17 条
[1]  
AKITA H, 1989, CHEM PHARM BULL, V37, P2876
[2]   THE EFFECT OF DIMETHYLSULFOXIDE ON THE ENANTIOSELECTIVITY IN THE PIG-LIVER ESTERASE CATALYZED-HYDROLYSIS OF DIALKYLATED PROPANEDIOIC ACID DIMETHYL ESTERS [J].
BJORKLING, F ;
BOUTELJE, J ;
GATENBECK, S ;
HULT, K ;
NORIN, T ;
SZMULIK, P .
BIOORGANIC CHEMISTRY, 1986, 14 (02) :176-181
[3]   THE HYDROLYSIS OF ETHYL 1-METHYL-2,4-CYCLOPENTADIENE-1-CARBOXYLATE BY NONENZYMATIC AND ENZYMATIC METHODS - CARBON-CARBON VS CARBON-OXYGEN BOND-CLEAVAGE [J].
BURGER, U ;
ERNEZELLWEGER, D ;
MAYERL, C .
HELVETICA CHIMICA ACTA, 1987, 70 (03) :587-592
[4]   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
[5]   2-AZETIDINONES - REACTION OF ALPHA-SILYLCARBANIONS WITH CARBONYL-COMPOUNDS [J].
GURTLER, S ;
OTTO, HH .
ARCHIV DER PHARMAZIE, 1989, 322 (02) :105-109
[6]   ENZYMATIC-HYDROLYSIS OF CYCLOPROPYL ACETATE, A FACILE METHOD FOR MEDIUM-SCALE AND LARGE-SCALE PREPARATIONS OF CYCLOPROPANOL [J].
JONGEJAN, JA ;
DUINE, JA .
TETRAHEDRON LETTERS, 1987, 28 (24) :2767-2768
[7]   ASYMMETRIC TRANSFORMATIONS CATALYZED BY ENZYMES IN ORGANIC-SOLVENTS [J].
KLIBANOV, AM .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) :114-120
[8]  
OHNO M, 1989, ORG REACTIONS, V37, P13
[9]  
PFULLER U, 1986, MIZELLEN VESIKEL MIK, P35
[10]  
SALCEDO J, 1983, ANAL BIOCHEM, V132, P168