ArticleChembiochem : a European journal of chemical biology2020
The l-Alanosine Gene Cluster Encodes a Pathway for Diazeniumdiolate Biosynthesis.
Article in Chembiochem : a European journal of chemical biology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed, 38 citations in OpenAlex.
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- Functional biosynthetic stereodivergence in a gene cluster via a dihydrosydnone N-oxide.Communications chemistry · 2024Article
- Chalkophomycin Biosynthesis Revealing Unique Enzyme Architecture for a Hybrid Nonribosomal Peptide Synthetase and Polyketide Synthase.Molecules (Basel, Switzerland) · 2024Article
- Tistrellabactins A and B Are PhotoreactiveJournal of natural products · 2023Article
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- Biosynthesis of the Unusual Carbon Skeleton of Nocuolin A.ACS chemical biology · 2022Article
- Biosynthesis of triacsin featuring an N-hydroxytriazene pharmacophore.Nature chemical biology · 2021Article
- Mitigation ofScience advances · 2021Article
- Leveraging Microbial Genomes and Genomic Context for Chemical Discovery.Accounts of chemical research · 2021Article
- In Vitro Reconstitution Reveals a Central Role for the N-Oxygenase PvfB in (Dihydro)pyrazine-N-oxide and Valdiazen Biosynthesis.Angewandte Chemie (International ed. in English) · 2020Article
- Flavin-dependent N-hydroxylating enzymes: distribution and application.Applied microbiology and biotechnology · 2020Review
- Nitric oxide as a source for bacterial triazole biosynthesis.Nature communications · 2020Article
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6 authors at 1 institution in 1 country.
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Abstract
N-Nitroso-containing natural products are bioactive metabolites with antibacterial and anticancer properties. In particular, compounds containing the diazeniumdiolate (N-nitrosohydroxylamine) group display a wide range of bioactivities ranging from cytotoxicity to metal chelation. Despite the importance of this structural motif, knowledge of its biosynthesis is limited. Herein we describe the discovery of a biosynthetic gene cluster in Streptomyces alanosinicus ATCC 15710 responsible for producing the diazeniumdiolate natural product l-alanosine. Gene disruption and stable isotope feeding experiments identified essential biosynthetic genes and revealed the source of the N-nitroso group. Additional biochemical characterization of the biosynthetic enzymes revealed that the non-proteinogenic amino acid l-2,3-diaminopropionic acid (l-Dap) is synthesized and loaded onto a free-standing peptidyl carrier protein (PCP) domain in l-alanosine biosynthesis, which we propose may be a mechanism of handling unstable intermediates generated en route to the diazeniumdiolate. These discoveries will facilitate efforts to determine the biochemistry of diazeniumdiolate formation.
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