期刊
NATURE COMMUNICATIONS
卷 12, 期 1, 页码 -出版社
NATURE RESEARCH
DOI: 10.1038/s41467-021-23206-9
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资金
- Israel Science Foundation [2333/19]
- Weizmann SABRA-Yeda-Sela-WRC Program
- Maurice and Vivienne Wohl Biology Endowment
- Israel Ministry of Absorption
- Estate of Emile Mimran
The study presents the thiol-assisted formation of guanidines, which can be used to design autocatalytic and oscillatory reaction networks. By utilizing nitrile-containing starting materials, an oscillator with oscillating concentration of a bicyclic derivative of dihydropyrimidine was created. The mixed thioester and thiouronium salt-based oscillator also showed unique responsiveness to chemical cues, expanding the toolbox for designing out-of-equilibrium chemical systems.
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. So far, only a few chemical oscillators based on organic reactions have been developed. Here, the authors report both autocatalytic and oscillatory reaction networks that form substituted guanidines from thiouronium salts; when coupled to cascade cyclization, this reaction network produces oscillations in the production of pyrimidine-based heterocycles.
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