ArticleAngewandte Chemie (International ed. in English)2016
Pinpointing a Mechanistic Switch Between Ketoreduction and "Ene" Reduction in Short-Chain Dehydrogenases/Reductases.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene.The Journal of organic chemistry · 2024Article
- Applications of Ene-Reductases in the Synthesis of Flavors and Fragrances.Journal of agricultural and food chemistry · 2024Review
- Article
- Biocatalytic Reduction Reactions from a Chemist's Perspective.Angewandte Chemie (International ed. in English) · 2021Review
- Crossing the Border: From Keto- to Imine Reduction in Short-Chain Dehydrogenases/Reductases.Chembiochem : a European journal of chemical biology · 2020Article
- Discovery, Characterisation, Engineering and Applications of Ene Reductases for Industrial Biocatalysis.ACS catalysis · 2019Article
- Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases.Angewandte Chemie (International ed. in English) · 2018Article
- Discovery of a Short-Chain Dehydrogenase from Catharanthus roseus that Produces a New Monoterpene Indole Alkaloid.Chembiochem : a European journal of chemical biology · 2018Article
- Engineering the "Missing Link" in Biosynthetic (-)-Menthol Production: Bacterial Isopulegone Isomerase.ACS catalysis · 2018Article
- Pinpointing a Mechanistic Switch Between Ketoreduction and "Ene" Reduction in Short-Chain Dehydrogenases/Reductases.Angewandte Chemie (International ed. in English) · 2016Article
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8 authors.
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Abstract
Three enzymes of the Mentha essential oil biosynthetic pathway are highly homologous, namely the ketoreductases (-)-menthone:(-)-menthol reductase and (-)-menthone:(+)-neomenthol reductase, and the "ene" reductase isopiperitenone reductase. We identified a rare catalytic residue substitution in the last two, and performed comparative crystal structure analyses and residue-swapping mutagenesis to investigate whether this determines the reaction outcome. The result was a complete loss of native activity and a switch between ene reduction and ketoreduction. This suggests the importance of a catalytic glutamate vs. tyrosine residue in determining the outcome of the reduction of α,β-unsaturated alkenes, due to the substrate occupying different binding conformations, and possibly also to the relative acidities of the two residues. This simple switch in mechanism by a single amino acid substitution could potentially generate a large number of de novo ene reductases.
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Registered trials
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