ArticleNucleic acids research2018
Principles of chemical geometry underlying chiral selectivity in RNA minihelix aminoacylation.
Article in Nucleic acids research, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 18 citations in OpenAlex.
- Origin of homochirality in terrestrial biology.Journal of biosciences · 2025Article
- Stereoselective RNA reaction with chiral 2'-OH acylating agents.Chemical science · 2023Article
- Mechanism of Chiral-Selective Aminoacylation of an RNA Minihelix Explored by QM/MM Free-Energy Simulations.Life (Basel, Switzerland) · 2023Article
- Acquisition of Dual Ribozyme-Functions in Nonfunctional Short Hairpin RNAs through Kissing-Loop Interactions.Life (Basel, Switzerland) · 2022Article
- Phosphorylation and sulfation share a common biosynthetic pathway, but extend biochemical and evolutionary diversity of biological macromolecules in distinct ways.Journal of the Royal Society, Interface · 2022Article
- The Coevolution of Biomolecules and Prebiotic Information Systems in the Origin of Life: A Visualization Model for Assembling the First Gene.Life (Basel, Switzerland) · 2022Review
- Peptide Bond Formation between Aminoacyl-Minihelices by a Scaffold Derived from the Peptidyl Transferase Center.Life (Basel, Switzerland) · 2022Article
- G:U-Independent RNA Minihelix Aminoacylation by Nanoarchaeum equitans Alanyl-tRNA Synthetase: An Insight into the Evolution of Aminoacyl-tRNA Synthetases.Journal of molecular evolution · 2020Article
- RNA Aptamers for a tRNA-Binding Protein fromLife (Basel, Switzerland) · 2020Article
- Perspectives on the Origin of Biological Homochirality on Earth.Journal of molecular evolution · 2019Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The origin of homochirality in L-amino acid in proteins is one of the mysteries of the evolution of life. Experimental studies show that a non-enzymatic aminoacylation reaction of an RNA minihelix has a preference for L-amino acid over D-amino acid. The reaction initiates by approaching of a 3'-oxygen of the RNA minihelix to the carbonyl carbon of an aminoacyl phosphate oligonucleotide. Here, employing molecular dynamics simulations, we examined the possible mechanisms that determine this chiral selectivity. The simulation system adopted a geometry required for the chemical reaction to occur more frequently with L-alanine than that with D-alanine. For L-alanine, the structure with this geometry was formed by a combination of stable dihedral angles along alanyl phosphate backbone with a canonical RNA structure, where the methyl group of alanine was placed on the opposite side of the approaching 3'-hydroxyl group with respect to the carbonyl plane. For D-alanine, the methyl group and the 3'-hydroxyl group were placed on the same side with respect to the carbonyl plane, which significantly decreased its ability to approach 3'-oxygen close to the carbonyl carbon compared to L-alanine. The mechanism suggested herein can explain experimentally observed chiral preferences.
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