Autocatalytic and oscillatory reaction networks that form guanidines and products of their cyclization

Alexander I. Novichkov, Anton I. Hanopolskyi, Xiaoming Miao, Linda J. W. Shimon, Yael Diskin-Posner and Sergey N. Semenov ()
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Alexander I. Novichkov: Weizmann Institute of Science
Anton I. Hanopolskyi: Weizmann Institute of Science
Xiaoming Miao: Weizmann Institute of Science
Linda J. W. Shimon: Weizmann Institute of Science
Yael Diskin-Posner: Weizmann Institute of Science
Sergey N. Semenov: Weizmann Institute of Science

Nature Communications, 2021, vol. 12, issue 1, 1-13

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-23206-9

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