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

J 2013

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

SZABLA, Rafal Kazimierz, Judit ŠPONEROVÁ, Jiří ŠPONER a Robert W. GORA

Základní údaje

Originální název

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

Autoři

SZABLA, Rafal Kazimierz, Judit ŠPONEROVÁ, Jiří ŠPONER a Robert W. GORA

Vydání

Physical Chemistry Chemical Physics, CAMBRIDGE, ROYAL SOC CHEMISTRY, 2013, 1463-9076

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.198

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1039/c3cp50320h

UT WoS

000318306100047

Klíčová slova anglicky

WATER-ASSISTED REACTION; AB-INITIO; PURINE NUCLEOSIDES; AMIDE HYDROLYSIS; PRIMITIVE EARTH; RNA WORLD; MODELS; ORIGIN; LIFE; SOLVATION

Štítky

ne MU

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 28. 6. 2013 13:30, Olga Křížová

Anotace

V originále

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.

Citovat

SZABLA, Rafal Kazimierz, Judit ŠPONEROVÁ, Jiří ŠPONER a 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, roč. 15, č. 20, s. 7812-7818. ISSN 1463-9076. Dostupné z: https://dx.doi.org/10.1039/c3cp50320h.

@article{1113609,
   author = {Szabla, Rafal Kazimierz and Šponerová, Judit and Šponer, Jiří and Gora, Robert W.},
   article_location = {CAMBRIDGE},
   article_number = {20},
   doi = {http://dx.doi.org/10.1039/c3cp50320h},
   keywords = {WATER-ASSISTED REACTION; AB-INITIO; PURINE NUCLEOSIDES; AMIDE HYDROLYSIS; PRIMITIVE EARTH; RNA WORLD; MODELS; ORIGIN; LIFE; SOLVATION},
   language = {eng},
   issn = {1463-9076},
   journal = {Physical Chemistry Chemical Physics},
   title = {Theoretical studies of the mechanism of 2-aminooxazole formation under prebiotically plausible conditions},
   url = {http://pubs.rsc.org/en/content/articlehtml/2013/cp/c3cp50320h},
   volume = {15},
   year = {2013}
}

TY  - JOUR
ID  - 1113609
AU  - Szabla, Rafal Kazimierz - Šponerová, Judit - Šponer, Jiří - Gora, Robert W.
PY  - 2013
TI  - Theoretical studies of the mechanism of 2-aminooxazole formation under prebiotically plausible conditions
JF  - Physical Chemistry Chemical Physics
VL  - 15
IS  - 20
SP  - 7812-7818
EP  - 7812-7818
PB  - ROYAL SOC CHEMISTRY
SN  - 14639076
KW  - WATER-ASSISTED REACTION
KW  - AB-INITIO
KW  - PURINE NUCLEOSIDES
KW  - AMIDE HYDROLYSIS
KW  - PRIMITIVE EARTH
KW  - RNA WORLD
KW  - MODELS
KW  - ORIGIN
KW  - LIFE
KW  - SOLVATION
UR  - http://pubs.rsc.org/en/content/articlehtml/2013/cp/c3cp50320h
L2  - http://pubs.rsc.org/en/content/articlehtml/2013/cp/c3cp50320h
N2  - 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.
ER  -

SZABLA, Rafal Kazimierz, Judit ŠPONEROVÁ, Jiří ŠPONER a Robert W. GORA. Theoretical studies of the mechanism of 2-aminooxazole formation under prebiotically plausible conditions. \textit{Physical Chemistry Chemical Physics}. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2013, roč.~15, č.~20, s.~7812-7818. ISSN~1463-9076. Dostupné z: https://dx.doi.org/10.1039/c3cp50320h.

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