ArticleNature communications2021
Autocatalytic and oscillatory reaction networks that form guanidines and products of their cyclization.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed.
- Designing soft materials through synthetic morphogenesis.Nature communications · 2026Article
- Autocatalytic cores in the diluted regime: classification and properties.Journal of mathematical biology · 2026Article
- Autonomous Spatiotemporal Regulation of Reversible Hydrogel Actuators by Chemical Reaction Networks.Advanced materials (Deerfield Beach, Fla.) · 2026Article
- Experimentally Guided Iterative Parameter Estimation for Predictive Chemical Oscillator Models.Angewandte Chemie (International ed. in English) · 2025Article
- Chemical waves in reaction-diffusion networks of small organic molecules.Chemical science · 2025Article
- Exploring the programmability of autocatalytic chemical reaction networks.Nature communications · 2024Article
- A Chemical Reaction Network Drives Complex Population Dynamics in Oscillating Self-Reproducing Vesicles.Journal of the American Chemical Society · 2024Article
- Evidence of Gas Phase Glucosyl Transfer and Glycation in the CID/HCD-Spectra of S-Glucosylated Peptides.International journal of molecular sciences · 2024Article
- Selenium catalysis enables negative feedback organic oscillators.Nature communications · 2024Article
- An oscillating reaction network with an exact closed form solution in the time domain.BMC bioinformatics · 2023Article
- Article
- Memory, switches, and an OR-port through bistability in chemically fueled crystals.Nature communications · 2022Article
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6 authors.
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Abstract
Autocatalytic and oscillatory networks of organic reactions are important for designing life-inspired materials and for better understanding the emergence of life on Earth; however, the diversity of the chemistries of these reactions is limited. In this work, we present the thiol-assisted formation of guanidines, which has a mechanism analogous to that of native chemical ligation. Using this reaction, we designed autocatalytic and oscillatory reaction networks that form substituted guanidines from thiouronium salts. The thiouronium salt-based oscillator show good stability of oscillations within a broad range of experimental conditions. By using nitrile-containing starting materials, we constructed an oscillator where the concentration of a bicyclic derivative of dihydropyrimidine oscillates. Moreover, the mixed thioester and thiouronium salt-based oscillator show unique responsiveness to chemical cues. The reactions developed in this work expand our toolbox for designing out-of-equilibrium chemical systems and link autocatalytic and oscillatory chemistry to the synthesis of guanidinium derivatives and the products of their transformations including analogs of nucleobases.
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