INFLUENCE OF STRUCTURAL FACTORS AND ENZYME TYPE ON THE REACTIVITY AND ENANTIOSELECTIVITY OF THE ENZYMATIC ESTERIFICATION OF BICYCLIC MESO DIALCOHOLS

被引：16
作者：
ASENSIO, G
ANDREU, C
MARCO, JA
机构：
[1] UNIV VALENCIA,FAC QUIM,E-46100 BURJASSOT,SPAIN
[2] UNIV VALENCIA,FAC FARM,DEPT QUIM ORGAN,E-46010 VALENCIA,SPAIN
来源：
CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 10期
关键词：
ENZYMES; LIPASES; DIALCOHOLS;
D O I：
10.1002/cber.19921251010
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The meso dialcohols 1 - 7 obtained from the Diels-Alder adducts furan/maleic anhydride, furan/dimethyl acetylenedicarboxylate, and cyclopentadiene/maleic anhydride, were subjected to enzymatic esterification in organic solvents. A mixture of the corresponding chiral monoacetates and the meso diacetates was obtained. It has been found that reaction rate and enantioselectivity markedly depend on substrate structure, temperature, enzyme type, and nature of the solvent. The presence of an oxygen bridge and an exo configuration are the tow structural features which lead to the highest enantioselectivity values.
引用
收藏
页码：2233 / 2238
页数：6
相关论文
共 41 条
[1]   DIE SYNTHESE DER STEREOISOMEREN ISO-SANTENE - DARSTELLUNG DES 2.3-DIMETHYLEN-1.4-ENDOMETHYLENCYCLOHEXANS UND SEINE UBERFUHRUNG IN SANTEN [J].
ALDER, K ;
ROTH, W .
CHEMISCHE BERICHTE-RECUEIL, 1955, 88 (03) :407-419
[2]   TANDEM CYCLOADDITION-ENZYMATIC TRANSESTERIFICATION - AN ENANTIOSELECTIVE DIELS-ALDER REACTION EQUIVALENT [J].
ANDREU, C ;
MARCO, JA ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3209-3210
[3]   ENANTIOSELECTIVE SYNTHESIS OF THE CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN-A BY A CHEMICOENZYMATIC APPROACH [J].
ARITA, M ;
ADACHI, K ;
ITO, Y ;
SAWAI, H ;
OHNO, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4049-4055
[4]   ENZYME-MEDIATED ENANTIOSELECTIVE ACYLATION OF SECONDARY-AMINES IN ORGANIC-SOLVENTS [J].
ASENSIO, G ;
ANDREU, C ;
MARCO, JA .
TETRAHEDRON LETTERS, 1991, 32 (33) :4197-4198
[5]   STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES [J].
BLOCH, R ;
GUIBEJAMPEL, E ;
GIRARD, C .
TETRAHEDRON LETTERS, 1985, 26 (34) :4087-4090
[6]   PREPARATION AND POLYMERISATION OF SOME BICYCLIC DIENES [J].
BOWE, MAP ;
MILLER, RGJ ;
ROSE, JB ;
WOOD, DGM .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (APR) :1541-1547
[7]   A SERINE PROTEASE TRIAD FORMS THE CATALYTIC CENTER OF A TRIACYLGLYCEROL LIPASE [J].
BRADY, L ;
BRZOZOWSKI, AM ;
DEREWENDA, ZS ;
DODSON, E ;
DODSON, G ;
TOLLEY, S ;
TURKENBURG, JP ;
CHRISTIANSEN, L ;
HUGEJENSEN, B ;
NORSKOV, L ;
THIM, L ;
MENGE, U .
NATURE, 1990, 343 (6260) :767-770
[8]   RECENT ADVANCES IN THE USE OF ENZYME-CATALYZED REACTIONS IN ORGANIC RESEARCH - THE SYNTHESIS OF BIOLOGICALLY-ACTIVE NATURAL-PRODUCTS AND ANALOGS [J].
BUTT, S ;
ROBERTS, SM .
NATURAL PRODUCT REPORTS, 1986, 3 (05) :489-503
[9]  
CALLANT P, 1984, TETRAHEDRON LETT, V25, P5797
[10]  
Carruthers W., 1990, CYCLOADDITION REACTI
12345