Structural and energetic factors controlling the
enantioselectivity of dinucleotide formation under prebiotic
conditions

J 2013

Structural and energetic factors controlling the enantioselectivity of dinucleotide formation under prebiotic conditions

ŠPONEROVÁ, Judit, Arnošt MLÁDEK a Jiří ŠPONER

Základní údaje

Originální název

Structural and energetic factors controlling the enantioselectivity of dinucleotide formation under prebiotic conditions

Autoři

ŠPONEROVÁ, Judit (348 Maďarsko, domácí), Arnošt MLÁDEK (203 Česká republika, domácí) a Jiří ŠPONER (203 Česká republika, garant, domácí)

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

Kód RIV

RIV/00216224:14740/13:00068748

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1039/c3cp44156c

UT WoS

000317012800013

Klíčová slova anglicky

APPROXIMATE COULOMB POTENTIALS; PEPTIDE-BOND FORMATION; ZETA VALENCE QUALITY; AUXILIARY BASIS-SETS; NA+-MONTMORILLONITE; RNA-SYNTHESIS; OLIGONUCLEOTIDE FORMATION; HETEROGENEOUS TEMPLATES; AMINO-ACIDS; AB-INITIO

Štítky

ok, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 11. 4. 2014 00:57, Olga Křížová

Anotace

V originále

Recently, it has been reported that the montmorillonite-catalyzed oligomerization of activated nucleotides exhibits remarkable enantioselectivity. In the current paper we investigate the structures and intrinsic energies of homochiral and heterochiral cyclic dinucleotides by means of accurate quantum chemical calculations in gas-phase and in bulk water. The steric effect of the clay is represented with geometrical constraints. Our computations reveal that the heterochiral dimer geometries are systematically less stable than their homochiral counterparts due to steric clashes inside the sugar-phosphate ring geometry. Thus we suggest that the homochiral selectivity observed in the cyclic dinucleotide formation in confined spaces may arise from the energetic destabilization of the heterochiral ring geometries as compared to their homochiral analogues. In the present paper we provide the first model of the 3D structure of D, L cyclic dinucleotides, which until now has eluded experimental observation.

Návaznosti

ED1.1.00/02.0068, projekt VaV

Název: CEITEC - central european institute of technology

Citovat

ŠPONEROVÁ, Judit, Arnošt MLÁDEK a Jiří ŠPONER. Structural and energetic factors controlling the enantioselectivity of dinucleotide formation under prebiotic conditions. Physical Chemistry Chemical Physics. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2013, roč. 15, č. 17, s. 6235-6242. ISSN 1463-9076. Dostupné z: https://dx.doi.org/10.1039/c3cp44156c.

@article{1114251,
   author = {Šponerová, Judit and Mládek, Arnošt and Šponer, Jiří},
   article_location = {CAMBRIDGE},
   article_number = {17},
   doi = {http://dx.doi.org/10.1039/c3cp44156c},
   keywords = {APPROXIMATE COULOMB POTENTIALS; PEPTIDE-BOND FORMATION; ZETA VALENCE QUALITY; AUXILIARY BASIS-SETS; NA+-MONTMORILLONITE; RNA-SYNTHESIS; OLIGONUCLEOTIDE FORMATION; HETEROGENEOUS TEMPLATES; AMINO-ACIDS; AB-INITIO},
   language = {eng},
   issn = {1463-9076},
   journal = {Physical Chemistry Chemical Physics},
   title = {Structural and energetic factors controlling the enantioselectivity of dinucleotide formation under prebiotic conditions},
   url = {http://pubs.rsc.org/en/content/articlepdf/2013/cp/c3cp44156c},
   volume = {15},
   year = {2013}
}

TY  - JOUR
ID  - 1114251
AU  - Šponerová, Judit - Mládek, Arnošt - Šponer, Jiří
PY  - 2013
TI  - Structural and energetic factors controlling the enantioselectivity of dinucleotide formation under prebiotic conditions
JF  - Physical Chemistry Chemical Physics
VL  - 15
IS  - 17
SP  - 6235-6242
EP  - 6235-6242
PB  - ROYAL SOC CHEMISTRY
SN  - 14639076
KW  - APPROXIMATE COULOMB POTENTIALS
KW  - PEPTIDE-BOND FORMATION
KW  - ZETA VALENCE QUALITY
KW  - AUXILIARY BASIS-SETS
KW  - NA+-MONTMORILLONITE
KW  - RNA-SYNTHESIS
KW  - OLIGONUCLEOTIDE FORMATION
KW  - HETEROGENEOUS TEMPLATES
KW  - AMINO-ACIDS
KW  - AB-INITIO
UR  - http://pubs.rsc.org/en/content/articlepdf/2013/cp/c3cp44156c
L2  - http://pubs.rsc.org/en/content/articlepdf/2013/cp/c3cp44156c
N2  - Recently, it has been reported that the montmorillonite-catalyzed oligomerization of activated nucleotides exhibits remarkable enantioselectivity. In the current paper we investigate the structures and intrinsic energies of homochiral and heterochiral cyclic dinucleotides by means of accurate quantum chemical calculations in gas-phase and in bulk water. The steric effect of the clay is represented with geometrical constraints. Our computations reveal that the heterochiral dimer geometries are systematically less stable than their homochiral counterparts due to steric clashes inside the sugar-phosphate ring geometry. Thus we suggest that the homochiral selectivity observed in the cyclic dinucleotide formation in confined spaces may arise from the energetic destabilization of the heterochiral ring geometries as compared to their homochiral analogues. In the present paper we provide the first model of the 3D structure of D, L cyclic dinucleotides, which until now has eluded experimental observation.
ER  -

ŠPONEROVÁ, Judit, Arnošt MLÁDEK a Jiří ŠPONER. Structural and energetic factors controlling the enantioselectivity of dinucleotide formation under prebiotic conditions. \textit{Physical Chemistry Chemical Physics}. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2013, roč.~15, č.~17, s.~6235-6242. ISSN~1463-9076. Dostupné z: https://dx.doi.org/10.1039/c3cp44156c.

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