Stereoselective reduction of ketones by Daucus carota hairy root cultures

被引:31
作者
Caron, D
Coughlan, AP
Simard, M
Bernier, J
Piché, Y
Chênevert, R
机构
[1] Univ Laval, Fac Sci & Genie, Dept Chim, CREFSIP, Quebec City, PQ G1K 7P4, Canada
[2] Univ Laval, Fac Foresterie & Geomat, Ctr Rech Biol Forestiere, Dept Sci Bois & Foret, Quebec City, PQ G1K 7P4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
acetophenone; Daucus carota; hairy root culture; (S)-phenylethanol; stereoselective reduction;
D O I
10.1007/s10529-005-5187-y
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Reduction of acetophenone by Daucus carota hairy root cultures afforded (S)-phenylethanol in high yield (96%) and excellent enantiomeric excess (ee >= 98%). Aromatic ketones, keto esters, and a simple aliphatic ketone were reduced with good stereoselectivity (ee = 62-98%) and moderate to high chemical yields (25-90%).
引用
收藏
页码:713 / 716
页数:4
相关论文
共 14 条
[1]   BIOCATALYTIC PREPARATION OF CHIRAL ALCOHOLS BY ENANTIOSELECTIVE REDUCTION WITH IMMOBILIZED CELLS OF CARROT [J].
AKAKABE, Y ;
TAKAHASHI, M ;
KAMEZAWA, M ;
KIKUCHI, K ;
TACHIBANA, H ;
OHTANI, T ;
NAOSHIMA, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (10) :1295-1298
[2]   Preparative synthesis of chiral alcohols by enantioselective reduction with Daucus carota root as biocatalyst [J].
Baldassarre, F ;
Bertoni, G ;
Chiappe, C ;
Marioni, F .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2000, 11 (01) :55-58
[3]   Highly stereoselective reduction of 4-Aryl-2-oxo but-3-enoic carboxylic esters by plant cell culture of Daucus carota [J].
Baskar, B ;
Ganesh, S ;
Lokeswari, TS ;
Chadha, A .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 27 (01) :13-17
[4]  
BECARD G, 1992, TECHNIQUES STUDY MYC, P89
[5]  
Cho BT, 2002, ALDRICHIM ACTA, V35, P3
[6]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[7]  
2-Z
[8]   Biotransformation using plant cultured cells [J].
Ishihara, K ;
Hamada, H ;
Hirata, T ;
Nakajima, N .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2003, 23 (2-6) :145-170
[9]   Recent advances in the biocatalytic reduction of ketones and oxidation of sec-alcohols [J].
Kroutil, W ;
Mang, H ;
Edegger, K ;
Faber, K .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2004, 8 (02) :120-126
[10]   Enantioselective reduction of bromo- and methoxy-acetophenone derivatives using carrot and celeriac enzymatic system [J].
Maczka, WK ;
Mironowicz, A .
TETRAHEDRON-ASYMMETRY, 2004, 15 (13) :1965-1967