AN INSIGHT INTO THE ACTIVE-SITE OF PSEUDOMONAS-FLUORESCENS (P-CEPACIA) LIPASE TO DEFINE THE STEREOCHEMICAL DEMAND FOR THE TRANSESTERIFICATION IN ORGANIC-SOLVENTS

被引:22
作者
FERRABOSCHI, P
CASATI, S
DEGRANDI, S
GRISENTI, P
SANTANIELLO, E
机构
[1] Dipartimento di Chimica e Biochimica Medica Via Saldini, 50-20133, Milano
来源
BIOCATALYSIS | 1994年 / 10卷 / 1-4期
关键词
PSEUDOMONAS FLUORESCENS LIPASE; PSEUDOMONAS CEPACIA LIPASE; ENZYMATIC TRANSESTERIFICATION; ENANTIOSELECTIVITY;
D O I
10.3109/10242429409065237
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The Pseudomonas fluorescens lipase-catalyzed transesterification of 2-methyl alkanols 1 and the 2-substituted oxiranemethanols 2 with vinyl acetate in organic solvents has been studied and the results discussed in terms of steric and electronic demand within the recently postulated models of the lipase active site.
引用
收藏
页码:279 / 288
页数:10
相关论文
共 30 条
[1]   FACILE ONE-POT TRANSFORMATION OF CARBOXYLIC-ACID CHLORIDES INTO 2-SUBSTITUTED ALLYL ALCOHOLS [J].
BARLUENGA, J ;
CONCELLON, JM ;
FERNANDEZSIMON, JL ;
YUS, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (08) :536-537
[2]   ENZYME-CATALYZED REACTIONS .17. LIPASE-CATALYZED RESOLUTION OF RACEMIC 2-ALKYL SUBSTITUTED 1-ALKANOLS [J].
BARTH, S ;
EFFENBERGER, F .
TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :823-833
[3]   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
[4]   CHEMOENZYMATIC SYNTHESIS OF THE C-13 SIDE-CHAIN OF TAXOL - OPTICALLY-ACTIVE 3-HYDROXY-4-PHENYL BETA-LACTAM DERIVATIVES [J].
BRIEVA, R ;
CRICH, JZ ;
SIH, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1068-1075
[5]   NITRILE OXIDES IN MEDICINAL CHEMISTRY .5. LIPASE PS-CATALYZED RESOLUTION OF A SET OF HETEROCYCLIC-DERIVATIVES [J].
CARREA, G ;
DEAMICI, M ;
DEMICHELI, C ;
LIVERANI, P ;
CARNIELLI, M ;
RIVA, S .
TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :1063-1072
[6]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[7]   ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS [J].
DEGUEILCASTAING, M ;
DEJESO, B ;
DROUILLARD, S ;
MAILLARD, B .
TETRAHEDRON LETTERS, 1987, 28 (09) :953-954
[8]   LIPASE-CATALYZED REACTIONS IN ORGANIC MEDIA - COMPETITION AND APPLICATIONS [J].
DELEUZE, H ;
LANGRAND, G ;
MILLET, H ;
BARATTI, J ;
BUONO, G ;
TRIANTAPHYLIDES, C .
BIOCHIMICA ET BIOPHYSICA ACTA, 1987, 911 (01) :117-120
[9]   SYNTHESIS OF CHIRAL BUILDING-BLOCKS FOR SELECTIVE ADENOSINE RECEPTOR AGENTS - LIPASE-CATALYZED RESOLUTION OF 2-BENZYLPROPANOL AND 2-BENZYLPROPIONIC ACID [J].
DELINCK, DL ;
MARGOLIN, AL .
TETRAHEDRON LETTERS, 1990, 31 (47) :6797-6798
[10]   THE MECHANISM OF HALIDE REDUCTIONS WITH LITHIUM ALUMINUM HYDRIDE .2. REDUCTION OF 2-CHLORO-2-PHENYLPROPIONIC ACID [J].
ELIEL, EL ;
FREEMAN, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (04) :923-928