BIOCATALYTIC PREPARATION OF CHIRAL ALCOHOLS BY ENANTIOSELECTIVE REDUCTION WITH IMMOBILIZED CELLS OF CARROT

被引:34
作者
AKAKABE, Y
TAKAHASHI, M
KAMEZAWA, M
KIKUCHI, K
TACHIBANA, H
OHTANI, T
NAOSHIMA, Y
机构
[1] OKAYAMA UNIV SCI,FAC SCI,DEPT BIOCHEM,OKAYAMA 700,JAPAN
[2] KONAN CHEM IND CO LTD,TAKATSUKI,OSAKA 569,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 10期
关键词
D O I
10.1039/p19950001295
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ability of immobilized cells of Daucus cal ota to reduce enantioselectively organic foreign substrates has been examined. The immobilized plant cells reduced, with excellent enantioselectivity, prochiral ketone substrates such as keto esters, aromatic ketones and heterocyclic aromatic ketones, leading to the corresponding chiral secondary alcohols with an enantiomeric purity of 52-99% ee in a chemical yield of 30-63%.
引用
收藏
页码:1295 / 1298
页数:4
相关论文
共 41 条
[1]   THE MECHANISTIC PATHWAY OF THE BIOTRANSFORMATION OF ACETOPHENONE BY IMMOBILIZED CELL-CULTURES OF GARDENIA [J].
AKAKABE, Y ;
NAOSHIMA, Y .
PHYTOCHEMISTRY, 1993, 32 (05) :1189-1191
[2]   BIOTRANSFORMATION OF ACETOPHENONE WITH IMMOBILIZED CELLS OF CARROT, TOBACCO AND GARDENIA [J].
AKAKABE, Y ;
NAOSHIMA, Y .
PHYTOCHEMISTRY, 1994, 35 (03) :661-664
[3]   BIOTRANSFORMATION OF MONOTERPENES BY MENTHA CELL-LINES - CONVERSION OF MENTHONE TO NEOMENTHOL [J].
AVIV, D ;
KROCHMAL, E ;
DANTES, A ;
GALUN, E .
PLANTA MEDICA, 1981, 42 (03) :236-243
[4]   PERMEABILIZATION OF IMMOBILIZED PLANT-CELLS, RESULTING IN RELEASE OF INTRACELLULARLY STORED PRODUCTS WITH PRESERVED CELL VIABILITY [J].
BRODELIUS, P ;
NILSSON, K .
EUROPEAN JOURNAL OF APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1983, 17 (05) :275-280
[5]   ALKYLATION OF ACETYL-METHYL ACETATE BY CHIRAL ALPHA-(P-NITROPHENYL)-ETHANOL WITH INTERMOLECULAR DEHYDRATION [J].
CABARET, D ;
MAIGROT, N ;
WELVART, Z .
TETRAHEDRON LETTERS, 1984, 25 (05) :547-550
[6]   BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].
CSUK, R ;
GLANZER, BI .
CHEMICAL REVIEWS, 1991, 91 (01) :49-97
[7]   ASYMMETRIC REDUCTION OF CARBONYL-COMPOUNDS BY YEAST .2. PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES [J].
DEOL, BS ;
RIDLEY, DD ;
SIMPSON, GW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (11) :2459-2467
[8]   STEREOSELECTIVE REDUCTION OF PROCHIRAL KETONES, USING ALUMINUM-HYDRIDE REAGENTS PREPARED FROM LIALH4 AND CHIRAL DIETHANOLAMINES [J].
DEVRIES, EFJ ;
BRUSSEE, J ;
KRUSE, CG ;
VANDERGEN, A .
TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :377-386
[9]   REDUCTION OF 4-SUBSTITUTED ACETOPHENONES BY YEAST [J].
EICHBERGER, G ;
FABER, K ;
GRIENGL, H .
MONATSHEFTE FUR CHEMIE, 1985, 116 (10) :1233-1236
[10]   MICROBIAL OXIDATION WITH BACILLUS-STEAROTHERMOPHILUS - HIGH ENANTIOSELECTIVE RESOLUTION OF 1-HETEROARYL AND 1-ARYL ALCOHOLS [J].
FANTIN, G ;
FOGAGNOLO, M ;
MEDICI, A ;
PEDRINI, P ;
POLI, S ;
GARDINI, F .
TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1607-1612