ArticleThe Journal of biological chemistry2011
Structure and function of the RedJ protein, a thioesterase from the prodiginine biosynthetic pathway in Streptomyces coelicolor.
Article in The Journal of biological chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 50 citations in OpenAlex.
- Enhancing the characteristics of phenolic acid decarboxylase via N-terminal substitution and investigating its immobilization.BMC biotechnology · 2025Article
- Optimization of Prodiginines as Single-Dose Curative Antimalarials.Journal of medicinal chemistry · 2025Article
- Effect of High-Temperature Stress on Fatty Acid Composition and Undecylprodiginine Biosynthesis inMicroorganisms · 2025Article
- Article
- The structure of the monobactam-producing thioesterase domain of SulM forms a unique complex with the upstream carrier protein domain.bioRxiv : the preprint server for biology · 2024Article
- Proteomic examination of polyester-polyurethane degradation by Streptomyces sp. PU10: Diverting polyurethane intermediates to secondary metabolite production.Microbial biotechnology · 2024Article
- Discrete Acyltransferases and Thioesterases in Iso-Migrastatin and Lactimidomycin Biosynthesis.Biochemistry · 2024Article
- Whole-genome sequencing-based characterization ofAccess microbiology · 2023Article
- Multiple Functions of the Type II Thioesterase Associated with the Phoslactomycin Polyketide Synthase.Biochemistry · 2022Article
- Thioesterase enzyme families: Functions, structures, and mechanisms.Protein science : a publication of the Protein Society · 2022Article
- Functional Analysis of an Acyltransferase-Like Domain from Polyunsaturated Fatty Acid Synthase in Thraustochytrium.Microorganisms · 2021Article
- Biosynthesis of depsipeptides, or Depsi: The peptides with varied generations.Protein science : a publication of the Protein Society · 2020Review
- The structural basis of N-acyl-α-amino-β-lactone formation catalyzed by a nonribosomal peptide synthetase.Nature communications · 2019Article
- Trapping biosynthetic acyl-enzyme intermediates with encoded 2,3-diaminopropionic acid.Nature · 2019Article
- YbtT is a low-specificity type II thioesterase that maintains production of the metallophore yersiniabactin in pathogenic enterobacteria.The Journal of biological chemistry · 2018Article
- Structure and Functional Analysis of ClbQ, an Unusual Intermediate-Releasing Thioesterase from the Colibactin Biosynthetic Pathway.ACS chemical biology · 2017Article
- MarH, a Bifunctional Enzyme Involved in the Condensation and Hydroxylation Steps of the Marineosin Biosynthetic Pathway.Organic letters · 2017Article
- Large-Scale Transposition Mutagenesis of Streptomyces coelicolor Identifies Hundreds of Genes Influencing Antibiotic Biosynthesis.Applied and environmental microbiology · 2017Article
- Role of Wax Ester Synthase/Acyl Coenzyme A:Diacylglycerol Acyltransferase in Oleaginous Streptomyces sp. Strain G25.Applied and environmental microbiology · 2016Article
- Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.Chemical reviews · 2016Review
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Authors and funding
8 authors at 3 institutions in 2 countries.
Funding
Abstract
Prodiginines are a class of red-pigmented natural products with immunosuppressant, anticancer, and antimalarial activities. Recent studies on prodiginine biosynthesis in Streptomyces coelicolor have elucidated the function of many enzymes within the pathway. However, the function of RedJ, which was predicted to be an editing thioesterase based on sequence similarity, is unknown. We report here the genetic, biochemical, and structural characterization of the redJ gene product. Deletion of redJ in S. coelicolor leads to a 75% decrease in prodiginine production, demonstrating its importance for prodiginine biosynthesis. RedJ exhibits thioesterase activity with selectivity for substrates having long acyl chains and lacking a β-carboxyl substituent. The thioesterase has 1000-fold greater catalytic efficiency with substrates linked to an acyl carrier protein (ACP) than with the corresponding CoA thioester substrates. Also, RedJ strongly discriminates against the streptomycete ACP of fatty acid biosynthesis in preference to RedQ, an ACP of the prodiginine pathway. The 2.12 Å resolution crystal structure of RedJ provides insights into the molecular basis for the observed substrate selectivity. A hydrophobic pocket in the active site chamber is positioned to bind long acyl chains, as suggested by a long-chain ligand from the crystallization solution bound in this pocket. The accessibility of the active site is controlled by the position of a highly flexible entrance flap. These data combined with previous studies of prodiginine biosynthesis in S. coelicolor support a novel role for RedJ in facilitating transfer of a dodecanoyl chain from one acyl carrier protein to another en route to the key biosynthetic intermediate 2-undecylpyrrole.
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