PLE CATALYZED HYDROLYZES OF ALPHA-SUBSTITUTED ALPHA-HYDROXY ESTERS - THE INFLUENCE OF THE SUBSTITUENTS

被引:25
作者
MOORLAG, H [1 ]
KELLOGG, RM [1 ]
机构
[1] UNIV GRONINGEN,DEPT ORGAN CHEM,NIJENBORGH 16,9747 AG GRONINGEN,NETHERLANDS
关键词
D O I
10.1016/S0957-4166(00)86125-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The enzymatic hydrolyses of a variety of alpha-substituted mandelic and lactic esters using pig liver esterase (PLE) have been investigated. High to moderate enantioselectivity was found for various alpha-substituted mandelic esters, whereas PLE showed low to no enantioselectivity for alpha-substituted lactic esters. We observed that the enantioselectivity of PLE depends strongly on the length and nature of the substituent at the alpha-position. Some consequences for an active site model of PLE are discussed.
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页码:705 / 720
页数:16
相关论文
共 25 条
[11]  
MOORLAG H, 1990, RECL TRAV CHIM PAY B, V109, P479
[12]   PIG-LIVER ESTERASE CATALYZED HYDROLYZES OF RACEMIC ALPHA-SUBSTITUTED ALPHA-HYDROXY ESTERS [J].
MOORLAG, H ;
KELLOGG, RM ;
KLOOSTERMAN, M ;
KAPTEIN, B ;
KAMPHUIS, J ;
SCHOEMAKER, HE .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5878-5881
[13]  
MOORLAG H, UNPUB
[14]   CONSTRUCTION OF NOVEL CHIRAL SYNTHONS WITH ENZYMES AND APPLICATION TO NATURAL PRODUCT SYNTHESIS .23. ENANTIOSELECTIVE HYDROLYSIS OF DIALKYL 3-MONOSUBSTITUTED GLUTARATES WITH PIG-LIVER ESTERASE - STRUCTURE-OPTICAL PURITY RELATIONSHIPS [J].
NAKADA, M ;
KOBAYASHI, S ;
OHNO, M ;
IWASAKI, S ;
OKUDA, S .
TETRAHEDRON LETTERS, 1988, 29 (32) :3951-3954
[15]   ENANTIOMERICALLY SELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYZES OF RACEMIC ALLENIC ESTERS [J].
RAMASWAMY, S ;
HUI, RAHF ;
JONES, JB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (20) :1545-1546
[16]  
ROBERTS DR, 1989, BEST SYNTHETIC METHO, pCH2
[17]   ENZYMES IN ORGANIC-SYNTHESIS .39. PREPARATIONS OF CHIRAL CYCLIC ACID-ESTERS AND BICYCLIC LACTONES VIA STEREOSELECTIVE PIG-LIVER ESTERASE CATALYZED HYDROLYZES OF CYCLIC MESO DIESTERS [J].
SABBIONI, G ;
JONES, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4565-4570
[18]  
STARING EGJ, 1986, RECL TRAV CHIM PAY B, V105, P374
[19]  
STARING EGJ, 1985, THESIS GRONINGEN
[20]   PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS USING ENZYMES .3. ENZYMATIC PREPARATION OF ENANTIOMERICALLY ENRICHED TERTIARY ALPHA-BENZYLOXY ACID-ESTERS - APPLICATION TO THE SYNTHESIS OF (S)-(-)-FRONTALIN [J].
SUGAI, T ;
KAKEYA, H ;
OHTA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4643-4647