ArticleJournal of the American Chemical Society2018
Chemistry of a Unique Polyketide-like Synthase.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 65 citations in OpenAlex.
- Hemolymph-Mediated Dynamics of Paralytic Shellfish Toxins and Tetrodotoxin in Scallops.Marine drugs · 2026Article
- Lysine acetylation in cyanobacteria: emerging mechanisms and functions.Biochemical Society transactions · 2025Review
- Structure-function analysis of carrier protein-dependent 2-sulfamoylacetyl transferase in the biosynthesis of altemicidin.Nature communications · 2024Article
- Synthesis of Saxitoxin Biosynthetic Intermediates: Reveal the Mechanism for Formation of its Tricyclic Skeleton in Biosynthesis.Chemistry, an Asian journal · 2024Article
- Metabolic Characteristics of Gut Microbiota and Insomnia: Evidence from a Mendelian Randomization Analysis.Nutrients · 2024Article
- PEARL-Catalyzed Peptide Bond Formation after Chain Reversal by Ureido-Forming Condensation Domains.ACS central science · 2024Article
- Why pyridoxal phosphate could be a functional predecessor of thiamine pyrophosphate and speculations on a primordial metabolism.RSC chemical biology · 2024Review
- Recent Advances in Cyanotoxin Synthesis and Applications: A Comprehensive Review.Microorganisms · 2023Review
- Mechanistic and Structural Insights into a Divergent PLP-Dependent l-Enduracididine Cyclase from a Toxic Cyanobacterium.ACS catalysis · 2023Article
- Versatile Chemo-Biocatalytic Cascade Driven by a Thermophilic and Irreversible C-C Bond-Forming α-Oxoamine Synthase.ACS sustainable chemistry & engineering · 2023Article
- Mechanistic and structural insights into a divergent PLP-dependent L-enduracididine cyclase from a toxic cyanobacterium.bioRxiv : the preprint server for biology · 2023Article
- Genetic association of toxin production in the dinoflagellateMicrobial genomics · 2022Article
- Understanding and Circumventing the Requirement for Native Thioester Substrates for α-Oxoamine Synthase Reactions.ACS chemical biology · 2022Article
- Structural Basis for Control of Methylation Extent in Polyketide Synthase Metal-DependentACS chemical biology · 2022Article
- First Identification of 12β-Deoxygonyautoxin 5 (12α-Gonyautoxinol 5) in the CyanobacteriumMarine drugs · 2022Article
- Chemoenzymatic Total Synthesis of Natural Products.Accounts of chemical research · 2021Review
- Biocatalytic, Stereoselective Deuteration of α-Amino Acids and Methyl Esters.ACS catalysis · 2020Article
- Broadening the scope of biocatalytic C-C bond formation.Nature reviews. Chemistry · 2020Article
- Substrate Promiscuity of a Paralytic Shellfish Toxin Amidinotransferase.ACS chemical biology · 2020Article
- Biosynthesis of Saxitoxin in Marine Dinoflagellates: An Omics Perspective.Marine drugs · 2020Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Like many complex natural products, the intricate architecture of saxitoxin (STX) has hindered full exploration of this scaffold's utility as a tool for studying voltage-gated sodium ion channels and as a pharmaceutical agent. Established chemical strategies can provide access to the natural product; however, a chemoenzymatic route to saxitoxin that could provide expedited access to related compounds has not been devised. The first step toward realizing a chemoenzymatic approach toward this class of molecules is the elucidation of the saxitoxin biosynthetic pathway. To date, a biochemical link between STX and its putative biosynthetic enzymes has not been demonstrated. Herein, we report the first biochemical characterization of any enzyme involved in STX biosynthesis. Specifically, the chemical functions of a polyketide-like synthase, SxtA, from the cyanobacteria Cylindrospermopsis raciborskii T3 are elucidated. This unique megasynthase is comprised of four domains: methyltransferase (MT), GCN5-related N-acetyltransferase (GNAT), acyl carrier protein (ACP), and the first example of an 8-amino-7-oxononanoate synthase (AONS) associated with a multidomain synthase. We have established that this single polypeptide carries out the formation of two carbon-carbon bonds, two decarboxylation events and a stereospecific protonation to afford the linear biosynthetic precursor to STX (4). The synthetic utility of the SxtA AONS is demonstrated by the synthesis of a suite of α-amino ketones from the corresponding α-amino acid in a single step.
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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.