ArticleJournal of the American Chemical Society2012
Amalgamation of nucleosides and amino acids in antibiotic biosynthesis: discovery of an L-threonine:uridine-5'-aldehyde transaldolase.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 69 citations in OpenAlex.
- Efficient production of glycine from glucose via a two-stage biosynthetic strategy.Microbial cell factories · 2026Article
- 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
- The TetR-like regulator Sco4385 and Crp-like regulator Sco3571 modulate heterologous production of antibiotics inApplied and environmental microbiology · 2025Article
- Biocatalytic asymmetric aldol addition into unactivated ketones.Nature chemistry · 2024Article
- Protein profiling and immunoinformatic analysis of the secretome of a metal-resistant environmental isolate Pseudomonas aeruginosa S-8.Folia microbiologica · 2024Article
- Secretome analysis and virulence assessment inJournal of oral microbiology · 2024Article
- Discovery of L-threonine transaldolases for enhanced biosynthesis of beta-hydroxylated amino acids.Communications biology · 2023Article
- Biosynthesis and Genome Mining Potentials of Nucleoside Natural Products.Chembiochem : a European journal of chemical biology · 2023Article
- β-Hydroxylation of α-amino-β-hydroxylbutanoyl-glycyluridine catalyzed by a nonheme hydroxylase ensures the maturation of caprazamycin.Communications chemistry · 2022Article
- Identification and characterization of enzymes involved in the biosynthesis of pyrimidine nucleoside antibiotics.Natural product reports · 2021Review
- Peculiarities of promiscuous L-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids.Applied microbiology and biotechnology · 2021Review
- l-Threonine Transaldolase Activity Is Enabled by a Persistent Catalytic Intermediate.ACS chemical biology · 2021Article
- Pyridoxal-5'-phosphate-dependent alkyl transfer in nucleoside antibiotic biosynthesis.Nature chemical biology · 2020Article
- An unusual metal-bound 4-fluorothreonine transaldolase from Streptomyces sp. MA37 catalyses promiscuous transaldol reactions.Applied microbiology and biotechnology · 2020Article
- Mechanism of action of nucleoside antibacterial natural product antibiotics.The Journal of antibiotics · 2019Review
- Recent advances in the biosynthesis of nucleoside antibiotics.The Journal of antibiotics · 2019Review
- The hidden enzymology of bacterial natural product biosynthesis.Nature reviews. Chemistry · 2019Article
- Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics.Journal of the American Chemical Society · 2019Article
- Biosynthetic and Synthetic Strategies for Assembling Capuramycin-Type Antituberculosis Antibiotics.Molecules (Basel, Switzerland) · 2019Review
- Proteomic Analysis and Virulence Assessment ofFrontiers in cellular and infection microbiology · 2019Article
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Authors and funding
10 authors at 3 institutions in 3 countries.
Funding
Abstract
The lipopeptidyl nucleoside antibiotics represented by A-90289, caprazamycin, and muraymycin are structurally highlighted by a nucleoside core that contains a nonproteinogenic β-hydroxy-α-amino acid named 5'-C-glycyluridine (GlyU). Bioinformatic analysis of the biosynthetic gene clusters revealed a shared open reading frame encoding a protein with sequence similarity to serine hydroxymethyltransferases, resulting in the proposal that this shared enzyme catalyzes an aldol-type condensation with glycine and uridine-5'-aldehyde to furnish GlyU. Using LipK involved in A-90289 biosynthesis as a model, we now functionally assign and characterize the enzyme responsible for the C-C bond-forming event during GlyU biosynthesis as an l-threonine:uridine-5'-aldehyde transaldolase. Biochemical analysis revealed this transformation is dependent upon pyridoxal-5'-phosphate, the enzyme has no activity with alternative amino acids, such as glycine or serine, as aldol donors, and acetaldehyde is a coproduct. Structural characterization of the enzyme product is consistent with stereochemical assignment as the threo diastereomer (5'S,6'S)-GlyU. Thus this enzyme orchestrates C-C bond breaking and formation with concomitant installation of two stereocenters to make a new l-α-amino acid with a nucleoside side chain.
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