Unknown

Dataset Information

0

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


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.

SUBMITTER: Novichkov AI 

PROVIDER: S-EPMC8138026 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC3251582 | biostudies-literature
| S-EPMC7870898 | biostudies-literature
| S-EPMC9491600 | biostudies-literature
| S-EPMC10458247 | biostudies-literature
| S-EPMC11310475 | biostudies-literature
| S-EPMC6030307 | biostudies-literature
| S-EPMC6424531 | biostudies-literature
| S-EPMC7126077 | biostudies-literature
| S-EPMC6408349 | biostudies-literature
| S-EPMC10321365 | biostudies-literature