Discovery of the Azaserine Biosynthetic Pathway Uncovers a Biological Route for α‐Diazoester Production
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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Discovery of the Azaserine Biosynthetic Pathway Uncovers a Biological Route for α‐Diazoester Production ; day:31 ; month:05 ; year:2023 ; extent:9
Angewandte Chemie / International edition. International edition ; (31.05.2023) (gesamt 9)
- Urheber
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Van Cura, Devon
Ng, Tai L.
Huang, Jing
Hager, Harry
Hartwig, John F.
Keasling, Jay D.
Balskus, Emily P.
- DOI
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10.1002/anie.202304646
- URN
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urn:nbn:de:101:1-2023060115061304937384
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 10:46 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Van Cura, Devon
- Ng, Tai L.
- Huang, Jing
- Hager, Harry
- Hartwig, John F.
- Keasling, Jay D.
- Balskus, Emily P.
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