ArticleNature chemical biology2020
Pyridoxal-5'-phosphate-dependent alkyl transfer in nucleoside antibiotic biosynthesis.
Article in Nature chemical biology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 44 citations in OpenAlex.
- Biosynthesis and enzymology of azaindane natural products.The Journal of antibiotics · 2026Review
- Biosynthesis of antibiotics with sulfonamide and azaindane moieties.The Journal of antibiotics · 2025Review
- Synthetic Biology in Natural Product Biosynthesis.Chemical reviews · 2025Review
- Molecular Basis for Cγ-N Bond Formation by PLP-Dependent Enzyme LolC.Biochemistry · 2024Article
- Discovery of a novel methionine biosynthetic routeApplied and environmental microbiology · 2024Article
- Decarboxylation in Natural Products Biosynthesis.JACS Au · 2024Review
- Discovery and Characterization of Pyridoxal 5'-Phosphate-Dependent Cycloleucine Synthases.Journal of the American Chemical Society · 2024Article
- Review
- Biosynthesis and Genome Mining Potentials of Nucleoside Natural Products.Chembiochem : a European journal of chemical biology · 2023Article
- Mechanistic and Structural Insights into a Divergent PLP-Dependent l-Enduracididine Cyclase from a Toxic Cyanobacterium.ACS catalysis · 2023Article
- Mechanistic and structural insights into a divergent PLP-dependent L-enduracididine cyclase from a toxic cyanobacterium.bioRxiv : the preprint server for biology · 2023Article
- Deciphering chemical logic of fungal natural product biosynthesis through heterologous expression and genome mining.Natural product reports · 2023Review
- Canavanine utilizationRSC chemical biology · 2022Article
- Noncanonical Functions of Enzyme Cofactors as Building Blocks in Natural Product Biosynthesis.JACS Au · 2022Review
- Biosynthesis of the Unusual Carbon Skeleton of Nocuolin A.ACS chemical biology · 2022Article
- β-Hydroxylation of α-amino-β-hydroxylbutanoyl-glycyluridine catalyzed by a nonheme hydroxylase ensures the maturation of caprazamycin.Communications chemistry · 2022Article
- Cryptic Phosphorylation-Mediated Divergent Biosynthesis of High-Carbon Sugar Nucleoside Antifungals.ACS chemical biology · 2022Article
- Article
- Enzymatic CJournal of the American Chemical Society · 2021Article
- Identification and characterization of enzymes involved in the biosynthesis of pyrimidine nucleoside antibiotics.Natural product reports · 2021Review
Corrections and comments
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Authors and funding
12 authors at 3 institutions in 3 countries.
Funding
Abstract
Several nucleoside antibiotics are structurally characterized by a 5″-amino-5″-deoxyribose (ADR) appended via a glycosidic bond to a high-carbon sugar nucleoside (5'S,6'S)-5'-C-glycyluridine (GlyU). GlyU is further modified with an N-alkylamine linker, the biosynthetic origin of which has yet to be established. By using a combination of feeding experiments with isotopically labeled precursors and characterization of recombinant proteins from multiple pathways, the biosynthetic mechanism for N-alkylamine installation for ADR-GlyU-containing nucleoside antibiotics has been uncovered. The data reveal S-adenosyl-L-methionine (AdoMet) as the direct precursor of the N-alkylamine, but, unlike conventional AdoMet- or decarboxylated AdoMet-dependent alkyltransferases, the reaction is catalyzed by a pyridoxal-5'-phosphate-dependent aminobutyryltransferase (ABTase) using a stepwise γ-replacement mechanism that couples γ-elimination of AdoMet with aza-γ-addition onto the disaccharide alkyl acceptor. In addition to using a conceptually different strategy for AdoMet-dependent alkylation, the newly discovered ABTases require a phosphorylated disaccharide alkyl acceptor, revealing a cryptic intermediate in the biosynthetic pathway.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.