Jump to main content
Jump to site search

Issue 45, 2017
Previous Article Next Article

Structural and electronic properties of barbituric acid and melamine-containing ribonucleosides as plausible components of prebiotic RNA: implications for prebiotic self-assembly

Author affiliations

Abstract

The RNA world hypothesis assumes that RNA was the first informational polymer that originated from prebiotic chemical soup. However, since the reaction of D-ribose with canonical nucleobases (A, C, G and U) fails to yield ribonucleosides (rNs) in substantial amounts, the spontaneous origin of rNs and the subsequent synthesis of RNA remains an unsolved mystery. To this end, it has been suggested that RNA may have evolved from primitive genetic material (preRNA) composed of simpler prebiotic heterocycles that spontaneously form glycosidic bonds with ribose. As an effort toward evaluating this hypothesis, the present study uses density functional theory (DFT) to assess the suitability of barbituric acid (BA) and melamine (MM) to act as prebiotic nucleobases, both of which have recently been shown to spontaneously form a glycosidic bond with ribose and organize into supramolecular assemblies in solution. The significant strength of hydrogen bonds involving BA and MM indicates that such interactions may have played a crucial role in their preferential selection over competing heterocycles that interact solely through stacking interactions from the primordial soup during the early phase of evolution. However, the greater stability of stacked dimers involving BA or MM and the canonical nucleobases compared to those consisting solely of BA and/or MM points towards the possible evolution of intermediate informational polymers consisting of prebiotic and canonical nucleobases, which could have eventually evolved into RNA. Analysis of the associated rNs reveals an anti conformational preference for the biologically-relevant β-anomer of both BA and MM rNs, which will allow complementary WC-like hydrogen bonding that can stabilize preRNA polymers. Large calculated deglycosylation barriers suggest BA rNs containing C–C glycosidic bonds are relevant in challenging prebiotic environments such as volcanic geotherms, while lower barriers indicate the MM rNs containing C–N–C glycosidic linkages may have been more likely synthesized from simple precursors such as urea-ice in icy (polar) regions. Together, our quantum chemical data clarifies the physicochemical interactions and stability of potential prebiotically-relevant constituents of BA and MM polymeric assemblies, and complements information from previous experimental studies to bolster the candidature of these heterocycles as prebiotic nucleobases.

Graphical abstract: Structural and electronic properties of barbituric acid and melamine-containing ribonucleosides as plausible components of prebiotic RNA: implications for prebiotic self-assembly

Back to tab navigation

Supplementary files

Publication details

The article was received on 07 Sep 2017, accepted on 06 Nov 2017 and first published on 06 Nov 2017


Article type: Paper
DOI: 10.1039/C7CP06123D
Citation: Phys. Chem. Chem. Phys., 2017,19, 30762-30771
  •   Request permissions

    Structural and electronic properties of barbituric acid and melamine-containing ribonucleosides as plausible components of prebiotic RNA: implications for prebiotic self-assembly

    S. Kaur, P. Sharma and S. D. Wetmore, Phys. Chem. Chem. Phys., 2017, 19, 30762
    DOI: 10.1039/C7CP06123D

Search articles by author

Spotlight

Advertisements