ArticleChembiochem : a European journal of chemical biology2019
Alteration of the Route to Menaquinone towards Isochorismate-Derived Metabolites.
Article in Chembiochem : a European journal of chemical biology, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed, 15 citations in OpenAlex.
- Engineering of the Thiamine Diphosphate-Dependent JanthE for the Synthesis of Tertiary Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Rutinosides-derived from Sarocladium strictum 6-O-α-rhamnosyl-β-glucosidase show enhanced anti-tumoral activity in pancreatic cancer cells.Microbial cell factories · 2024Article
- Biosynthesis of Menaquinone in E. coli: Identification of an Elusive Isomer of SEPHCHC.Chembiochem : a European journal of chemical biology · 2022Article
- Targeted accumulation of selective anticancer depsipeptides by reconstructing the precursor supply in the neoantimycin biosynthetic pathway.Bioresources and bioprocessing · 2021Article
- Alteration of the Route to Menaquinone towards Isochorismate-Derived Metabolites.Chembiochem : a European journal of chemical biology · 2019Article
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9 authors at 3 institutions in 2 countries.
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Abstract
Chorismate and isochorismate constitute branch-point intermediates in the biosynthesis of many aromatic metabolites in microorganisms and plants. To obtain unnatural compounds, we modified the route to menaquinone in Escherichia coli. We propose a model for the binding of isochorismate to the active site of MenD ((1R,2S, 5S,6S)-2-succinyl-5-enolpyruvyl-6-hydroxycyclohex-3-ene-1-carboxylate (SEPHCHC) synthase) that explains the outcome of the native reaction with α-ketoglutarate. We have rationally designed variants of MenD for the conversion of several isochorismate analogues. The double-variant Asn117Arg-Leu478Thr preferentially converts (5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate (2,3-trans-CHD), the hydrolysis product of isochorismate, with a >70-fold higher ratio than that for the wild type. The single-variant Arg107Ile uses (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylate (2,3-trans-CHA) as substrate with >6-fold conversion compared to wild-type MenD. The novel compounds have been made accessible in vivo (up to 5.3 g L
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