ArticleAngewandte Chemie (International ed. in English)2023
Discovery of the Azaserine Biosynthetic Pathway Uncovers a Biological Route for α-Diazoester Production.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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25 citing papers in PubMed, 46 citations in OpenAlex.
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- Chemoenzymatic Triazolopyridine Synthesis Enabled by Cryptic Diazo Formation by Vanadium-Dependent Haloperoxidases.Organic letters · 2026Article
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- Chemoenzymatic Diazo Synthesis Enabled by Enzymatic Halide Recycling with Vanadium-Dependent Haloperoxidases.Journal of the American Chemical Society · 2026Article
- Expanding the Terpene Universe: Synthetic Biology and Non-Natural Chemistry in Engineered Microorganisms.Molecules (Basel, Switzerland) · 2025Review
- Characterization of the N-Hydroxylating Monooxygenase TheA from Thermocrispum agreste Reveals a Broad Substrate Spectrum.Chembiochem : a European journal of chemical biology · 2025Article
- Identification of a l-Threonine-Utilizing Hydrazine Synthetase for Thrazarine Biosynthesis in Streptomyces coerulescens MH802-fF5.Chembiochem : a European journal of chemical biology · 2025Article
- Exploring the metabolic signaling network of GFPT in cancer.Cell death discovery · 2025Review
- Denitrogenative Alkylation of K-Ras(G12D) Inhibits Oncogenic Signaling in Cancer Cells.Journal of the American Chemical Society · 2025Article
- Structural Basis for the Catalytic Mechanism of ATP-Dependent Diazotase CmaA6.Angewandte Chemie (International ed. in English) · 2025Article
- Heme Oxygenase-Like Metalloenzymes.Annual review of biochemistry · 2025Review
- A new heme enzyme family forms hydrazine groups in diverse biosynthetic pathways.bioRxiv : the preprint server for biology · 2025Article
- Formation of Carboxymethyl-Phosphotriester Adducts in DNA.Chemical research in toxicology · 2025Article
- Synthetic Biology in Natural Product Biosynthesis.Chemical reviews · 2025Review
- Revision of the Formycin A and Pyrazofurin Biosynthetic Pathways Reveals Specificity for d-Glutamic Acid and a CrypticJournal of the American Chemical Society · 2025Article
- Synthesis of Substituted Acyclic and Cyclic N-Alkylhydrazines by Enzymatic Reductive Hydrazinations.Chembiochem : a European journal of chemical biology · 2025Article
- Recent Developments and Challenges in the Enzymatic Formation of Nitrogen-Nitrogen Bonds.ACS catalysis · 2025Review
- Production of Phenyldiazene Derivatives Using the Biosynthetic Pathway of an Aromatic Diazo Group-Containing Natural Product from an Actinomycete.Chembiochem : a European journal of chemical biology · 2025Article
- Effective Targeting of Glutamine Synthetase with Amino Acid Analogs as a Novel Therapeutic Approach in Breast Cancer.International journal of molecular sciences · 2024Article
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Authors and funding
7 authors at 4 institutions in 2 countries.
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Abstract
Azaserine is a bacterial metabolite containing a biologically unusual and synthetically enabling α-diazoester functional group. Herein, we report the discovery of the azaserine (aza) biosynthetic gene cluster from Glycomyces harbinensis. Discovery of related gene clusters reveals previously unappreciated azaserine producers, and heterologous expression of the aza gene cluster confirms its role in azaserine assembly. Notably, this gene cluster encodes homologues of hydrazonoacetic acid (HYAA)-producing enzymes, implicating HYAA in α-diazoester biosynthesis. Isotope feeding and biochemical experiments support this hypothesis. These discoveries indicate that a 2-electron oxidation of a hydrazonoacetyl intermediate is required for α-diazoester formation, constituting a distinct logic for diazo biosynthesis. Uncovering this biological route for α-diazoester synthesis now enables the production of a highly versatile carbene precursor in cells, facilitating approaches for engineering complete carbene-mediated biosynthetic transformations in vivo.
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