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

被引：41

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

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