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

Durchschein K, Wallner S, Macheroux P, Schwab W, Winkler T, Kreis W, Faber K (2012)

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Publication Language: English

Publication Type: Journal article, Original article

Publication year: 2012

Journal

Publisher: Wiley-VCH Verlag

Book Volume: 2012

Pages Range: 4963-4968

Journal Issue: 26

DOI: 10.1002/ejoc.201200776

Abstract

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 5β-reductase (At5β-StR) from Arabidopsis thaliana (thale cress) and leukotriene B 4 12-hydroxydehydrogenase (LTB 4DH/PGR) from Rattus norvegicus (rat) appear to be promising candidates, in particular for the asymmetric bioreduction of open-chain enals, nitroalkenes and α,β-unsaturated γ-butyrolactones. Competing nitro reduction and non-enzymatic Weitz-Scheffer epoxidation were largely suppressed. Electronically activated alkenes have been stereoselectively reduced by using a single-enzyme-cofactor system employing nicotinamide-dependent non-flavin ene reductases. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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How to cite

APA:

Durchschein, K., Wallner, S., Macheroux, P., Schwab, W., Winkler, T., Kreis, W., & Faber, K. (2012). Nicotinamide-Dependent Ene Reductases as Alternative Biocatalysts for the Reduction of Activated Alkenes. European Journal of Organic Chemistry, 2012(26), 4963-4968. https://doi.org/10.1002/ejoc.201200776

MLA:

Durchschein, Katharina, et al. "Nicotinamide-Dependent Ene Reductases as Alternative Biocatalysts for the Reduction of Activated Alkenes." European Journal of Organic Chemistry 2012.26 (2012): 4963-4968.

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