ReviewInternational journal of molecular sciences2011
Molecular basis for chiral selection in RNA aminoacylation.
Review in International journal of molecular sciences, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
6 citing papers in PubMed, 22 citations in OpenAlex.
- Biophysical Interactions Underpin the Emergence of Information in the Genetic Code.Life (Basel, Switzerland) · 2023Article
- Determining the Diastereoselectivity of the Formation of Dipeptidonucleotides by NMR Spectroscopy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Principles of chemical geometry underlying chiral selectivity in RNA minihelix aminoacylation.Nucleic acids research · 2018Article
- Origins and Early Evolution of the tRNA Molecule.Life (Basel, Switzerland) · 2015Review
- Article
- Ribosome evolution: emergence of peptide synthesis machinery.Journal of biosciences · 2011Review
Corrections and comments
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Authors and funding
1 author at 1 institution in 1 country.
Funding
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Abstract
The chiral-selective aminoacylation of an RNA minihelix is a potential progenitor to modern tRNA-based protein synthesis using l-amino acids. This article describes the molecular basis for this chiral selection. The extended double helical form of an RNA minihelix with a CCA triplet (acceptor of an amino acid), an aminoacyl phosphate donor nucleotide (mimic of aminoacyl-AMP), and a bridging nucleotide facilitates chiral-selective aminoacylation. Energetically, the reaction is characterized by a downhill reaction wherein an amino acid migrates from a high-energy acyl phosphate linkage to a lower-energy carboxyl ester linkage. The reaction occurs under the restriction that the nucleophilic attack of O, from 3'-OH in the terminal CCA, to C, from C=O in the acyl phosphate linkage, must occur at a Bürgi-Dunitz angle, which is defined as the O-C=O angle of approximately 105°. The extended double helical form results in a steric hindrance at the side chain of the amino acid leading to chiral preference combined with cation coordinations in the amino acid and the phosphate oxygen. Such a system could have developed into the protein biosynthetic system with an exclusively chiral component (l-amino acids) via (proto) ribosomes.
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Registered trials
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