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

SZABLA, Rafal Kazimierz, Judit ŠPONEROVÁ, Jiří ŠPONER and Robert W. GORA. Theoretical studies of the mechanism of 2-aminooxazole formation under prebiotically plausible conditions. Physical Chemistry Chemical Physics. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2013, vol. 15, No 20, p. 7812-7818. ISSN 1463-9076. Available from: https://dx.doi.org/10.1039/c3cp50320h.

Basic information

• Original name: Theoretical studies of the mechanism of 2-aminooxazole formation under prebiotically plausible conditions
• Authors: SZABLA, Rafal Kazimierz, Judit ŠPONEROVÁ, Jiří ŠPONER and Robert W. GORA.
• Edition: Physical Chemistry Chemical Physics, CAMBRIDGE, ROYAL SOC CHEMISTRY, 2013, 1463-9076.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10403 Physical chemistry
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 4.198
• Organization unit: Central European Institute of Technology
• Doi: http://dx.doi.org/10.1039/c3cp50320h
• UT WoS: 000318306100047
• Keywords in English: WATER-ASSISTED REACTION; AB-INITIO; PURINE NUCLEOSIDES; AMIDE HYDROLYSIS; PRIMITIVE EARTH; RNA WORLD; MODELS; ORIGIN; LIFE; SOLVATION
• Tags: ne MU
• Tags: International impact, Reviewed

Abstract

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.