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
[11]   ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].
EVANS, DA ;
ENNIS, MD ;
MATHRE, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739
[12]   A CHEMOENZYMATIC SYNTHESIS OF ENANTIOMERICALLY PURE (R)-2-METHYLDECAN-1-OL AND (S)-2-METHYLDECAN-1-OL [J].
FERRABOSCHI, P ;
GRISENTI, P ;
MANZOCCHI, A ;
SANTANIELLO, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (09) :1159-1161
[13]   ENZYMATIC RESOLUTION OF 2-SUBSTITUTED OXIRANEMETHANOLS, A CLASS OF SYNTHETICALLY USEFUL BUILDING-BLOCKS BEARING A CHIRAL QUATERNARY CENTER [J].
FERRABOSCHI, P ;
BREMBILLA, D ;
GRISENTI, P ;
SANTANIELLO, E .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5478-5480
[14]   LIPASE-CATALYZED RESOLUTION OF ACYCLIC AMINO ALCOHOL PRECURSORS [J].
FOELSCHE, E ;
HICKEL, A ;
HONIG, H ;
SEUFERWASSERTHAL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1749-1753
[15]   CONVENIENT PRACTICAL RESOLUTION OF RACEMIC ALKYL-ARYL ALCOHOLS VIA ENZYMATIC ACYLATION WITH SUCCINIC ANHYDRIDE IN ORGANIC-SOLVENTS [J].
GUTMAN, AL ;
BRENNER, D ;
BOLTANSKI, A .
TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :839-844
[16]   PHEROMONE SYNTHESIS .76. SYNTHESIS OF THE ENANTIOMERS OF 14-METHYL-1-OCTADECENE, THE SEX-PHEROMONE OF THE PEACH LEAFMINER MOTH [J].
KATO, M ;
MORI, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1985, 49 (08) :2479-2480
[17]   A RULE TO PREDICT WHICH ENANTIOMER OF A SECONDARY ALCOHOL REACTS FASTER IN REACTIONS CATALYZED BY CHOLESTEROL ESTERASE, LIPASE FROM PSEUDOMONAS-CEPACIA, AND LIPASE FROM CANDIDA-RUGOSA [J].
KAZLAUSKAS, RJ ;
WEISSFLOCH, ANE ;
RAPPAPORT, AT ;
CUCCIA, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2656-2665
[18]  
KLYNE W, 1974, ATLAS STEREOCHEMISTR, P26
[19]   ENZYMIC PREPARATION OF ENANTIOMERICALLY PURE SECONDARY ALCOHOLS - ESTER SYNTHESIS BY IRREVERSIBLE ACYL TRANSFER USING A HIGHLY SELECTIVE ESTER HYDROLASE FROM PSEUDOMONAS SP - AN ATTRACTIVE ALTERNATIVE TO ESTER HYDROLYSIS [J].
LAUMEN, K ;
BREITGOFF, D ;
SCHNEIDER, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (22) :1459-1461
[20]   SYNTHESIS OF 3-KETO-4-DIAZO-5-ALPHA-DIHYDROSTEROIDS AS POTENTIAL IRREVERSIBLE INHIBITORS OF STEROID 5-ALPHA-REDUCTASE [J].
METCALF, BW ;
JUND, K ;
BURKHART, JP .
TETRAHEDRON LETTERS, 1980, 21 (01) :15-18