Nicotinamide-Dependent Ene Reductases as Alternative Biocatalysts for the Reduction of Activated Alkenes

被引：40

作者：

Durchschein, Katharina ^{[1
]}

Wallner, Silvia ^{[2
]}

Macheroux, Peter ^{[2
]}

Schwab, Wilfried ^{[3
]}

Winkler, Thorsten ^{[4
]}

Kreis, Wolfgang ^{[5
]}

Faber, Kurt ^{[1
]}

机构：

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

[2] Graz Univ Technol, Inst Biochem, A-8010 Graz, Austria

[3] Tech Univ Munich, D-80333 Munich, Germany

[4] Univ Dusseldorf, Inst Mol Enzyme Technol, Res Ctr Julich, D-52426 Julich, Germany

[5] Univ Erlangen Nurnberg, Dept Biol, D-91058 Erlangen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 26期

基金：

奥地利科学基金会;

关键词：

Alkenes; Reduction; Biotransformations; Enzymes; OLD YELLOW ENZYME; C=C-BONDS; ASYMMETRIC BIOREDUCTION; ENOATE REDUCTASES; PROGESTERONE; 5-BETA-REDUCTASE; CULTURED-CELLS; CDNA CLONING; OXIDOREDUCTASE; PURIFICATION; EXPRESSION;

D O I：

10.1002/ejoc.201200776

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four NAD(P)H-dependent non-flavin ene reductases have been investigated for their ability to reduce activated C=C bonds in an asymmetric fashion by using 20 structurally diverse substrates. In comparison with flavin-dependent Old Yellow Enzyme homologues, a higher degree of electronic activation was required, because the best activities were obtained with enals and nitroalkenes rather than enones and carboxylic esters. Although FaEO from Fragaria x ananassa (strawberry) and its homologue SlEO from Solanum lycopersicum (tomato) exhibited a narrow substrate spectrum, progesterone 5 beta-reductase (At5 beta-StR) from Arabidopsis thaliana (thale cress) and leukotriene B4 12-hydroxydehydrogenase (LTB4DH/PGR) from Rattus norvegicus (rat) appear to be promising candidates, in particular for the asymmetric bioreduction of open-chain enals, nitroalkenes and alpha,beta-unsaturated gamma-butyrolactones. Competing nitro reduction and non-enzymatic WeitzScheffer epoxidation were largely suppressed.

引用

页码：4963 / 4968

页数：6

共 5 条

[1] Stereoconvergent Reduction of Activated Alkenes by a Nicotinamide Free Synergistic Photobiocatalytic System
Wang, Yajie
Huang, Xiaoqiang
Hui, Jingshu
Vo, Lam Tung
Zhao, Huimin
ACS CATALYSIS, 2020, 10 (16) : 9431 - 9437
[2] An ene reductase from Clavispora lusitaniae for asymmetric reduction of activated alkenes
Ni, Yan
Yu, Hui-Lei
Lin, Guo-Qiang
Xu, Jian-He
ENZYME AND MICROBIAL TECHNOLOGY, 2014, 56 : 40 - 45
[3] Overcoming Co-Product Inhibition in the Nicotinamide Independent Asymmetric Bioreduction of Activated C=C-Bonds Using Flavin- Dependent Ene-Reductases
Winkler, Christoph K.
Clay, Dorina
van Heerden, Esta
Faber, Kurt
BIOTECHNOLOGY AND BIOENGINEERING, 2013, 110 (12) : 3085 - 3092
[4] Recombinant Δ4,5-Steroid 5β-Reductases as Biocatalysts for the Reduction of Activated C=C-Double Bonds in Monocyclic and Acyclic Molecules
Burda, Edyta
Krausser, Marina
Fischer, Gabriele
Hummel, Werner
Mueller-Uri, Frieder
Kreis, Wolfgang
Groeger, Harald
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) : 2787 - 2790
[5] Reduction of Activated Carbon-Carbon Double Bonds using Highly Active and Enantioselective Double Bond Reductases ENEs from Johnson Matthey's enzyme collection provide a suitable alternative to metal-catalysed hydrogenation
Dominguez, Beatriz
Schell, Ursula
Bisagni, Serena
Kalthoff, Thomas
JOHNSON MATTHEY TECHNOLOGY REVIEW, 2016, 60 (04): : 243 - 249

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