Synthesis of enantiopure epoxides through biocatalytic approaches

被引:122
作者
Archelas, A
Furstoss, R
机构
[1] Groupe Biocatalyse et Chimie Fine, ERS 157 Associée au CNRS, Fac. des Sciences de Luminy, 13288 Marseille Cedex 9, Case 901
关键词
chiral epoxides; biotransformations; epoxidation; epoxide hydrolysis;
D O I
10.1146/annurev.micro.51.1.491
中图分类号
Q93 [微生物学];
学科分类号
071005 ; 100705 ;
摘要
Enantiopure epoxides, as well as their corresponding vicinal diols, are valuable intermediates in fine organic synthesis, in particular for the preparation of biologically active compounds. The necessity of preparing such target molecules in an optically pure form has triggered much research, leading to the emergence of various new methods based on either conventional chemistry or enzymatically catalyzed reactions. In this review, we focus on the biocatalytic approaches, which include direct epoxidation of olefinic double bonds as well as indirect biocatalytic methods, and which allow for the synthesis of these important chiral building blocks in enantiomerically enriched or even enantiopure form.
引用
收藏
页码:491 / 525
页数:35
相关论文
共 176 条
[1]   OXIDATION OF 1-ALKENES TO 1,2-EPOXYALKANES BY PSEUDOMONAS-OLEOVORANS [J].
ABBOTT, BJ ;
HOU, CT .
APPLIED MICROBIOLOGY, 1973, 26 (01) :86-91
[2]   HIGHLY ENANTIOSELECTIVE EPOXIDATION OF DISUBSTITUTED ALKENES WITH HYDROGEN-PEROXIDE CATALYZED BY CHLOROPEROXIDASE [J].
ALLAIN, EJ ;
HAGER, LP ;
DENG, L ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4415-4416
[3]  
ALLEN RH, 1969, J BIOL CHEM, V244, P2078
[4]  
Arand M, 1996, J BIOL CHEM, V271, P4223
[5]   MICROBIOLOGICAL TRANSFORMATIONS .30. ENANTIOSELECTIVE HYDROLYSIS OF RACEMIC EPOXIDES - THE SYNTHESIS OF ENANTIOPURE INSECT JUVENILE-HORMONE ANALOGS (BOWERS COMPOUND) [J].
ARCHELAS, A ;
DELBECQUE, JP ;
FURSTOSS, R .
TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2445-2446
[6]   SYNTHESIS OF OPTICALLY PURE PITYOL - A PHEROMONE OF THE BARK BEETLE PITYOPHTHORUS-PITYOGRAPHUS - USING A CHEMOENZYMATIC ROUTE [J].
ARCHELAS, A ;
FURSTOSS, R .
TETRAHEDRON LETTERS, 1992, 33 (36) :5241-5242
[7]  
ARCHELAS A, 1988, BIOCATALYSIS, V1, P283
[8]   TOTAL SYNTHESIS OF (+)-LEUKOTRIENE B4 METHYL-ESTER AND ITS 5-EPIMER FROM (R)-GLYCIDOL [J].
AVIGNONTROPIS, M ;
TREILHOU, M ;
POUGNY, JR ;
FRECHARDORTUNO, I ;
LINSTRUMELLE, G .
TETRAHEDRON, 1991, 47 (35) :7279-7286
[9]   RESONANCE RAMAN STUDIES OF ISOTOPICALLY LABELED CHLOROPEROXIDASE [J].
BANGCHAROENPAURPONG, O ;
CHAMPION, PM ;
HALL, KS ;
HAGER, LP .
BIOCHEMISTRY, 1986, 25 (09) :2374-2378
[10]   DIFFERENT ENANTIOSELECTIVITY AND REGIOSELECTIVITY OF THE CYTOSOLIC AND MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF SIMPLE PHENYL-SUBSTITUTED EPOXIDES [J].
BELLUCCI, G ;
CHIAPPE, C ;
CORDONI, A ;
MARIONI, F .
TETRAHEDRON LETTERS, 1994, 35 (24) :4219-4222