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Boosting photobioredox catalysis by morpholine electron donors under aerobic conditions
TU Wien, Inst Appl Synthet Chem, Getreidemarkt 9 163, A-1060 Vienna, Austria.
TU Wien, Inst Appl Synthet Chem, Getreidemarkt 9 163, A-1060 Vienna, Austria.
TU Wien, Inst Appl Synthet Chem, Getreidemarkt 9 163, A-1060 Vienna, Austria.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry. Department of Chemistry, Qena Faculty of Science, South Valley University, 83523 Qena, Egypt.
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2019 (English)In: Catalysis Science & Technology, ISSN 2044-4753, E-ISSN 2044-4761, Vol. 9, no 10, p. 2682-2688Article in journal (Refereed) Published
Abstract [en]

Light-driven reduction of flavins, e.g. FAD or FMN, by sacrificial electron donors emerged as a convenient method to promote biocatalytic transformations. However, flavin activation has been restricted to oxygen-free conditions to prevent enzyme deactivation caused by reactive oxygen species (ROS). Herein, we show that the photoreduction of FMN by morpholines, including 3-(N-morpholino)propanesulfonic acid (MOPS), lessens the deactivation of the enoate reductase XenB from Pseudomonas sp. during the stereoselective asymmetric enzymatic reduction of a model ,-unsaturated diketone under aerobic conditions, leading to a 91% GC-yield and a stereoselectivity greater than 94%. The kinetic stability of the thermolabile XenB was increased by more than 20-fold in MOPS buffer compared to that in Tris-HCl buffer, and a pronounced positive effect on the transition midpoint temperature was observed. The reactive form of the FMN photocatalyst is stabilized by the formation of a (3)[FMN--MOPS+] ensemble, which reduces the formation of hydrogen peroxide and other ROS in the presence of oxygen. These results contribute to broaden the application of photobiocatalytic transformations using flavin-dependent reductases.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2019. Vol. 9, no 10, p. 2682-2688
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Biochemistry and Molecular Biology
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URN: urn:nbn:se:uu:diva-390605DOI: 10.1039/c9cy00496cISI: 000472455800023OAI: oai:DiVA.org:uu-390605DiVA, id: diva2:1342238
Available from: 2019-08-13 Created: 2019-08-13 Last updated: 2019-08-13Bibliographically approved

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Sá, Jacinto

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