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

0392589 - BFÚ 2014 RIV GB eng J - Článek v odborném periodiku
Šponer, Judit E. - Mládek, Arnošt - Šponer, Jiří
Structural and energetic factors controlling the enantioselectivity of dinucleotide formation under prebiotic conditions.
Physical Chemistry Chemical Physics. Roč. 15, č. 17 (2013), s. 6235-6242. ISSN 1463-9076. E-ISSN 1463-9084
Grant CEP: GA ČR GAP208/10/2302
Grant ostatní: GA MŠk(CZ) ED1.1.00/02.0068
Program: ED
Výzkumný záměr: CEZ:AV0Z50040702
Institucionální podpora: RVO:68081707
Klíčová slova: APPROXIMATE COULOMB POTENTIALS * PEPTIDE-BOND FORMATION * ZETA VALENCE QUALITY
Kód oboru RIV: BO - Biofyzika
Impakt faktor: 4.198, rok: 2013

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
Trvalý link: http://hdl.handle.net/11104/0221409