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Molecular Basis for Chiral Selection in RNA Aminoacylation
Department of Biological Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan
Research Institute for Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan
PRESTO, Japan Science and Technology Agency, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
Received: 24 May 2011; in revised form: 29 June 2011 / Accepted: 18 July 2011 / Published: 22 July 2011
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.
Keywords: homochirality; amino acid; RNA; aminoacylation; stereochemistry; extended double helix; origin of life
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MDPI and ACS Style
Tamura, K. Molecular Basis for Chiral Selection in RNA Aminoacylation. Int. J. Mol. Sci. 2011, 12, 4745-4757.
Tamura K. Molecular Basis for Chiral Selection in RNA Aminoacylation. International Journal of Molecular Sciences. 2011; 12(7):4745-4757.
Tamura, Koji. 2011. "Molecular Basis for Chiral Selection in RNA Aminoacylation." Int. J. Mol. Sci. 12, no. 7: 4745-4757.