Publication details

Theoretical studies of the mechanism of 2-aminooxazole formation under prebiotically plausible conditions

Authors

SZABLA Rafal Kazimierz ŠPONEROVÁ Judit ŠPONER Jiří GORA Robert W.

Year of publication 2013
Type Article in Periodical
Magazine / Source Physical Chemistry Chemical Physics
MU Faculty or unit

Central European Institute of Technology

Citation
Web http://pubs.rsc.org/en/content/articlehtml/2013/cp/c3cp50320h
Doi http://dx.doi.org/10.1039/c3cp50320h
Field Physical chemistry and theoretical chemistry
Keywords WATER-ASSISTED REACTION; AB-INITIO; PURINE NUCLEOSIDES; AMIDE HYDROLYSIS; PRIMITIVE EARTH; RNA WORLD; MODELS; ORIGIN; LIFE; SOLVATION
Description 2-Aminooxazole is generally considered to play a central role in the origin of informational polymers. In the current contribution we use density functional calculations to investigate the detailed mechanism of 2-aminooxazole formation from the prebiotic soup according to the scenario suggested by M. W. Powner, B. Gerland and J. D. Sutherland, Nature, 2009, 459, 239-242. Parallel to the phosphate-catalyzed reaction pathway we also describe its water-assisted variant. Our calculations show that phosphate-catalysis is indispensable not only in the cyclization and the subsequent water-elimination steps, as previously suggested, but also in the very first reaction step leading to the formation of the carbinolamine intermediate. In addition, we suggest concurrent reaction channels for the cyclization and water-elimination reaction steps, both involving catalytic phosphate ions.