ArticleACS chemical biology2012
Biosynthesis of albomycin δ(2) provides a template for assembling siderophore and aminoacyl-tRNA synthetase inhibitor conjugates.
Article in ACS chemical biology, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed, 65 citations in OpenAlex.
- Ferrichrome: bacterial function, synthetic mimics, and biomedical applications.Frontiers in microbiology · 2026Review
- Characterization of C3' Epimerization of the Thioheptose Core in the Biosynthesis of AlbomycinACS catalysis · 2025Article
- Biosynthesis of the Thiofuranose Core in Albomycin Requires a Versatile Enzyme AbmG That Catalyzes Net Dehydration via Cryptic Phosphorylation.Journal of the American Chemical Society · 2025Article
- RadicalNature catalysis · 2025Article
- Discovery of acylsulfenic acid-featuring natural product sulfenicin and characterization of its biosynthesis.Nature chemistry · 2025Article
- A New Albomycin-Producing Strain ofInsects · 2022Article
- The chemistry and biology of natural ribomimetics and related compounds.RSC chemical biology · 2022Review
- Biosynthesis and Chemical Synthesis of Albomycin Nucleoside Antibiotics.Antibiotics (Basel, Switzerland) · 2022Review
- Identification and characterization of enzymes involved in the biosynthesis of pyrimidine nucleoside antibiotics.Natural product reports · 2021Review
- Natural Trojan horse inhibitors of aminoacyl-tRNA synthetases.RSC chemical biology · 2021Review
- Aminoacyl-tRNA Synthetases as Valuable Targets for Antimicrobial Drug Discovery.International journal of molecular sciences · 2021Review
- Platform to Discover Protease-Activated Antibiotics and Application to Siderophore-Antibiotic Conjugates.Journal of the American Chemical Society · 2020Article
- Recent developments in self-resistance gene directed natural product discovery.Natural product reports · 2020Review
- Identification of the Enzymes Mediating the Maturation of the Seryl-tRNA Synthetase Inhibitor SB-217452 during the Biosynthesis of Albomycins.Angewandte Chemie (International ed. in English) · 2020Article
- Engineering nucleoside antibiotics toward the development of novel antimicrobial agents.The Journal of antibiotics · 2019Review
- Theranostic Gallium Siderophore Ciprofloxacin Conjugate with Broad Spectrum Antibiotic Potency.Journal of medicinal chemistry · 2019Article
- The Role of Iron and Siderophores in Infection, and the Development of Siderophore Antibiotics.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2019Article
- Crossroads of Antibiotic Resistance and Biosynthesis.Journal of molecular biology · 2019Review
- Progress and challenges in aminoacyl-tRNA synthetase-based therapeutics.The Journal of biological chemistry · 2019Review
- Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics.Journal of the American Chemical Society · 2019Article
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8 authors at 2 institutions in 1 country.
Funding
Abstract
"Trojan horse" antibiotic albomycins are peptidyl nucleosides consisting of a highly modified 4'-thiofuranosyl cytosine moiety and a ferrichrome siderophore that are linked by a peptide bond via a serine residue. While the latter component serves to sequester iron from the environment, the seryl nucleoside portion is a potent inhibitor of bacterial seryl-tRNA synthetases, resulting in broad-spectrum antimicrobial activities of albomycin δ(2). The isolation of albomycins has revealed this biological activity is optimized only following two unusual cytosine modifications, N4-carbamoylation and N3-methylation. We identified a genetic locus (named abm) for albomycin production in Streptomyces sp. ATCC 700974. Gene deletion and complementation experiments along with bioinformatic analysis suggested 18 genes are responsible for albomycin biosynthesis and resistance, allowing us to propose a potential biosynthetic pathway for installing the novel chemical features. The gene abmI, encoding a putative methyltransferase, was functionally assigned in vitro and shown to modify the N3 of a variety of cytosine-containing nucleosides and antibiotics such as blasticidin S. Furthermore, a ΔabmI mutant was shown to produce the descarbamoyl-desmethyl albomycin analogue, supporting that the N3-methylation occurs before the N4-carbamoylation in the biosynthesis of albomycin δ(2). The combined genetic information was utilized to identify an abm-related locus (named ctj) from the draft genome of Streptomyces sp. C. Cross-complementation experiments and in vitro studies with CtjF, the AbmI homologue, suggest the production of a similar 4'-thiofuranosyl cytosine in this organism. In total, the genetic and biochemical data provide a biosynthetic template for assembling siderophore-inhibitor conjugates and modifying the albomycin scaffold to generate new derivatives.
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