Chemo- and stereo-selective biocatalytic reduction of α,β-unsaturated ketones employing a chemo-tolerant ADH from Rhodococcus ruber DSM 44541

被引：23

作者：

van Deursen, R ^{[1
]}

Stampfer, W ^{[1
]}

Edegger, K ^{[1
]}

Faber, K ^{[1
]}

Kroutil, W ^{[1
]}

机构：

[1] Graz Univ, Dept Chem Organ & Bioorgan Chem, A-8010 Graz, Austria

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2004年 / 31卷 / 4-6期

基金：

奥地利科学基金会;

关键词：

chemoselective; stereoselective; biocatalytic reduction; Rhodococcus ruber;

D O I：

10.1016/j.molcatb.2004.09.004

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：

Biocatalytic reduction of the keto-moiety of alpha,beta-unsaturated ketones (enones) was achieved with absolute chemo- and stereo-selectivity employing whole lyophilized cells of Rhodococcus ruber DSM 44541 to furnish the corresponding allylic alcohols in e.e. up to >99%. It was shown that a stereocenter in gamma-position of the ketone moiety to be reduced is too distant from the reaction center to induce any significant diastereoselectivity, thus no kinetic resolution of an racemic ketone occurred. (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：159 / 163

页数：5

共 26 条

[1] LACTOBACILLUS-KEFIR ALCOHOL-DEHYDROGENASE - A USEFUL CATALYST FOR SYNTHESIS [J].

BRADSHAW, CW ;

HUMMEL, W ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1532-1536

[2] A PSEUDOMONAS SP ALCOHOL-DEHYDROGENASE WITH BROAD SUBSTRATE-SPECIFICITY AND UNUSUAL STEREOSPECIFICITY FOR ORGANIC-SYNTHESIS [J].

BRADSHAW, CW ;

FU, H ;

SHEN, GJ ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1526-1532

[3] Enzyme-mediated synthesis of (R)- and (S)-α-ionone [J].

Brenna, E ;

Fuganti, C ;

Grasselli, P ;

Redaelli, M ;

Serra, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (24) :4129-4134

[4] A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and α,β-unsaturated ketones [J].

Burk, MJ ;

Hems, W ;

Herzberg, D ;

Malan, C ;

Zanotti-Gerosa, A .

ORGANIC LETTERS, 2000, 2 (26) :4173-4176

[5]

Faber K., 2004, BIOTRANSFORMATIONS O, P205

[6] Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: complementary approaches [J].

Hage, A ;

Petra, DGI ;

Field, JA ;

Schipper, D ;

Wijnberg, JBPA ;

Kamer, PCJ ;

Reek, JNH ;

van Leeuwen, PWNM ;

Wever, R ;

Schoemaker, HE .

TETRAHEDRON-ASYMMETRY, 2001, 12 (07) :1025-1034

[7] MICROBIOLOGICAL REDUCTION OF ALPHA,BETA-UNSATURATED KETONES BY BEAUVERIA-SULFURESCENS [J].

KERGOMARD, A ;

RENARD, MF ;

VESCHAMBRE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (05) :792-798

[8] Purification and characterization of a chemotolerant alcohol dehydrogenase applicable to coupled redox reactions [J].

Kosjek, B ;

Stampfer, W ;

Pogorevc, M ;

Goessler, W ;

Faber, K ;

Kroutil, W .

BIOTECHNOLOGY AND BIOENGINEERING, 2004, 86 (01) :55-62

[9] A new protocol for a regioselective aldol condensation as an alternative convenient synthesis of β-ketols and α,β-unsaturated ketones [J].

Kourouli, T ;

Kefalas, P ;

Ragoussis, N ;

Ragoussis, V .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4615-4618

[10] Bacterial epoxide hydrolases of opposite enantiopreference [J].

Krenn, W ;

Osprian, I ;

Kroutil, W ;

Braunegg, G ;

Faber, K .

BIOTECHNOLOGY LETTERS, 1999, 21 (08) :687-690

← 1 2 3 →