ArticleJournal of the American Chemical Society2013
EcdGHK are three tailoring iron oxygenases for amino acid building blocks of the echinocandin scaffold.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed.
- Active-site recognition enables hydroxylation of a fluorine-deactivated C-H bond in 6,6,6-trifluoro-L-norleucine.Chemical communications (Cambridge, England) · 2026Article
- A Novel Cyclopentane Pyridine Compound Identified from Saccharothrix syringae NRRL B-16468 by PPTase-Based Activation.Current microbiology · 2026Article
- In-Silico and Functional Characterization of EcdLp, an ABC Transporter of Aspergillus nidulans NRRL11440.Current microbiology · 2026Article
- Regulation and induction of fungal secondary metabolites: a comprehensive review.Archives of microbiology · 2025Review
- Metabolic engineering ofSynthetic and systems biotechnology · 2025Article
- The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.Chemical reviews · 2025Review
- Efficient chemoenzymatic synthesis of α-aryl aldehydes as intermediates in C-C bond forming biocatalytic cascades.ACS catalysis · 2022Article
- Echinocandins Localized to the Target-Harboring Cell Surface Are Not Degraded but Those Entering the Vacuole Are.ACS chemical biology · 2022Article
- Benzylic Dehydroxylation of Echinocandin Antifungal Drugs Restores Efficacy against Resistance Conferred by Mutated Glucan Synthase.Journal of the American Chemical Society · 2022Article
- Branching and converging pathways in fungal natural product biosynthesis.Fungal biology and biotechnology · 2022Review
- Discovery of cyclohexadepsipeptides with anti-Zika virus activities and biosynthesis of the nonproteinogenic building block (3S)-methyl-l-proline.The Journal of biological chemistry · 2021Article
- Reinvigorating the Chiral Pool: Chemoenzymatic Approaches to Complex Peptides and Terpenoids.Accounts of chemical research · 2021Review
- l-Threonine Transaldolase Activity Is Enabled by a Persistent Catalytic Intermediate.ACS chemical biology · 2021Article
- Echinocandins: structural diversity, biosynthesis, and development of antimycotics.Applied microbiology and biotechnology · 2021Review
- Exploration of Iron- and a-Ketoglutarate-Dependent Dioxygenases as Practical Biocatalysts in Natural Product Synthesis.Synlett : accounts and rapid communications in synthetic organic chemistry · 2021Article
- Elevated Vacuolar Uptake of Fluorescently Labeled Antifungal Drug Caspofungin Predicts Echinocandin Resistance in Pathogenic Yeast.ACS central science · 2020Article
- Enzyme evolution in fungal indole alkaloid biosynthesis.The FEBS journal · 2020Review
- Apc.LaeA and Apc.VeA of the velvet complex govern secondary metabolism and morphological development in the echinocandin-producing fungus Aspergillus pachycristatus.Journal of industrial microbiology & biotechnology · 2020Article
- Disruption of stcA blocks sterigmatocystin biosynthesis and improves echinocandin B production in Aspergillus delacroxii.World journal of microbiology & biotechnology · 2019Article
- Targeted Rediscovery and Biosynthesis of the Farnesyl-Transferase Inhibitor Pepticinnamin E.Chembiochem : a European journal of chemical biology · 2019Article
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6 authors.
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Abstract
The echinocandins are a small group of fungal N-acylated cyclic hexapeptides that are fungicidal for candida strains and fungistatic for aspergilli by targeting cell wall 1,3-β-glucan synthases. The side chains of all six amino acid building blocks have hydroxyl groups, including the nonproteinogenic 4R,5R-dihydroxy-Orn1, 4R-OH-Pro3, 3S,4S-dihydroxy-homoTyr4, and 3S-OH-4S-Me-Pro6. The echinocandin (ecd) gene cluster contains two predicted nonheme mononuclear iron oxygenase genes (ecdG,K) and one encoding a P450 type heme protein (ecdH). Deletion of the ecdH gene in the producing strain Emericella rugulosa generates an echinocandin scaffold (echinocandin D) lacking both hydroxyl groups on Orn1. Correspondingly, the ΔecdG strain failed to hydroxylate C3 of the homoTyr residue, and purified EcdG hydroxylated free L-homoTyr at C3. The ΔecdK strain failed to generate mature echinocandin unless supplemented with either 4R-Me-Pro or 3S-OH-4S-Me-Pro, indicating blockage of a step upstream of Me-Pro formation. Purified EcdK is a Leu 5-hydroxylase, acting iteratively at C5 to yield γ-Me-Glu-γ-semialdehyde in equilibrium with the cyclic imine product. Evaluation of deshydroxyechinocandin scaffolds in the in vitro anticandidal assays revealed up to a 3-fold loss of potency for the ΔecdG scaffolds, but a 3-fold gain of potency for the ΔecdH scaffold, in line with prior results on deoxyechinocandin homologues.
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