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 and Jiří ŠPONER

Basic information

Original name

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

Authors

ŠPONEROVÁ, Judit (348 Hungary, belonging to the institution), Arnošt MLÁDEK (203 Czech Republic, belonging to the institution) and Jiří ŠPONER (203 Czech Republic, guarantor, belonging to the institution)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.198

RIV identification code

RIV/00216224:14740/13:00068748

Organization unit

Central European Institute of Technology

DOI

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

UT WoS

000317012800013

Keywords in English

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

Abstract

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.

Links

ED1.1.00/02.0068, research and development project

Name: CEITEC - central european institute of technology

Citovat

ŠPONEROVÁ, Judit, Arnošt MLÁDEK and Jiří ŠPONER. Structural and energetic factors controlling the enantioselectivity of dinucleotide formation under prebiotic conditions. Physical Chemistry Chemical Physics. CAMBRIDGE: ROYAL SOC CHEMISTRY, 2013, vol. 15, No 17, p. 6235-6242. ISSN 1463-9076. Available from: 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 and 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, vol.~15, No~17, p.~6235-6242. ISSN~1463-9076. Available from: https://dx.doi.org/10.1039/c3cp44156c.

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