ArticleJournal of the American Chemical Society2024
Discovery and Characterization of Pyridoxal 5'-Phosphate-Dependent Cycloleucine Synthases.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Biosynthesis and enzymology of azaindane natural products.The Journal of antibiotics · 2026Review
- Emerging enzymatic strategies for the synthesis of α-tertiary amino acids.Communications chemistry · 2026Review
- Role of Vitamin B₆ in Testosterone Synthesis.The world journal of men's health · 2026Review
- Pyridoxal 5'-Phosphate-Dependent Enzymatic Decarboxylative Annulation.Journal of the American Chemical Society · 2026Article
- Microbial unusual gene clusters without prominent core enzymes: natural products, biosynthesis and genome mining.The Journal of antibiotics · 2026Review
- Microcrystal Electron Diffraction-Guided Discovery of Fungal Metabolites.Journal of the American Chemical Society · 2025Article
- α-Hydrazino Acids Inhibit Pyridoxal Phosphate-Dependent Decarboxylases via "Catalytically Correct" Ketoenamine Tautomers: A Special Motif for Chemical Biology and Drug Discovery?ACS catalysis · 2025Article
- Article
- Molecular Basis for Cγ-N Bond Formation by PLP-Dependent Enzyme LolC.Biochemistry · 2024Article
Corrections and comments
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Authors and funding
10 authors.
Funding
Abstract
Pyridoxal 5'-phosphate (PLP)-dependent enzymes are the most versatile biocatalysts for synthesizing nonproteinogenic amino acids. α,α-Disubstituted quaternary amino acids, such as 1-aminocyclopentane-1-carboxylic acid (cycloleucine), are useful building blocks for pharmaceuticals. In this study, starting with the biosynthesis of fusarilin A, we discovered a family of PLP-dependent enzymes that can facilitate tandem carbon-carbon forming steps to catalyze an overall [3 + 2]-annulation. In the first step, the cycloleucine synthases use SAM as the latent electrophile and an in situ-generated enamine as the nucleophile for γ-substitution. Whereas previously characterized γ-replacement enzymes protonate the resulting α-carbon and release the acyclic amino acid, cycloleucine synthases can catalyze an additional, intramolecular aldol or Mannich reaction with the nucleophilic α-carbon to form the substituted cyclopentane. Overall, the net [3 + 2]-annulation reaction can lead to 2-hydroxy or 2-aminocycloleucine products. These studies further expand the biocatalytic scope of PLP-dependent enzymes.
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Registered trials
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