ArticleNature communications2025
Molecular basis for azetidine-2-carboxylic acid biosynthesis.
Article in Nature communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Directed biosynthesis of the designer peptidyl nucleoside antibiotics featuring a simplified azetidine-containing moiety.Synthetic and systems biotechnology · 2027Article
- S-Adenosyl-d-Methionine as a Non-Physiological Substrate for a Wide Range of SAM-Dependent Enzymes.Chembiochem : a European journal of chemical biology · 2026Article
- Azetidine-2-carboxylic acid-induced oligodendrogliopathy in vitro and the pathogenesis of multiple sclerosis.Journal of neuropathology and experimental neurology · 2026Article
- Triplet Energy Transfer-Driven Intermolecular [2+2] Photocycloaddition of Acyclic Imines and Indoles: Facile Access to Azetidine-Fused Indolines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- 4″-Methyl-ACS chemical biology · 2026Article
- Discovery and Mechanism of a Diiron Enzyme in Ethylidene Azetidine Formation.Journal of the American Chemical Society · 2025Article
- Plant amino acid analogues as antimicrobial agents.Amino acids · 2025Review
- Structural Basis for 3-Amino-3-carboxypropyl Transfer in Nocardicin Biosynthesis.Journal of the American Chemical Society · 2025Article
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
Azetidine-2-carboxylic acid (AZE) is a long-known plant metabolite. Recently, AZE synthases have been identified in bacterial natural product pathways involving non-ribosomal peptide synthetases. AZE synthases catalyse the intramolecular 4-exo-tet cyclisation of S-adenosylmethionine (SAM), yielding a highly strained heterocycle. Here, we combine structural and biochemical analyses with quantum mechanical calculations and mutagenesis studies to reveal catalytic insights into AZE synthases. The cyclisation of SAM is facilitated by an exceptional substrate conformation and supported by desolvation effects as well as cation-π interactions. In addition, we uncover related SAM lyases in diverse bacterial phyla, suggesting a wider prevalence of AZE-containing metabolites than previously expected. To explore the potential of AZE as a proline mimic in combinatorial biosynthesis, we introduce an AZE synthase into the pyrrolizixenamide pathway and thereby engineer analogues of azabicyclenes. Taken together, our findings provide a molecular framework to understand and exploit SAM-dependent cyclisation reactions.
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Registered trials
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