Biological catalysis involves interactions distant from the site of chemistry that can position the substrate for reaction. Catalysis of RNA 2'-O-transphosphorylation by the hepatitis delta virus (HDV) ribozyme is sensitive to the identity of the N(-1) nucleotide flanking the reactive phosphoryl group. However, the interactions that affect the conformation of this position, and in turn the 2'O nucleophile, are unclear. Here, we describe the application of multiple substrate internal competition kinetic analyses to understand how the N(-1) nucleobase contributes to HDV catalysis and test the utility of this approach for RNA structure-function studies. Internal competition reactions containing all four substrate sequence variants at the N(-1) position in reactions using ribozyme active site mutations at A77 and A78 were used to test a proposed base-pairing interaction. Mutants A78U, A78G, and A79G retain significant catalytic activity but do not alter the specificity for the N(-1) nucleobase. Effects of nucleobase analog substitutions at N(-1) indicate that U is preferred due to the ability to donate an H-bond in the Watson-Crick face and avoid minor groove steric clash. The results provide information essential for evaluating models of the HDV active site and illustrate multiple substrate kinetic analyses as a practical approach for characterizing structure-function relationships in RNA reactions.
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http://dx.doi.org/10.1016/j.ab.2015.04.024 | DOI Listing |
ACS Omega
March 2024
Departamento de Física y Química Teórica, Facultad de Química, Universidad Nacional Autónoma de México, CDMX 04510, Mexico.
The possible role of radical species in the formation of the long-lived triplet states observed for 2-thiocytosine upon UV irradiation was theoretically investigated. It is predicted that the radical fragments arising from the homolytic rupture of the NH group of the thiobase can be yielded upon ultraviolet-A radiation. Recombination of the radicals through the most favorable singlet channel yields the lowest-lying tautomer of the 2-thiocytosine (the amino-thiol form) through a barrierless pathway.
View Article and Find Full Text PDFSci Rep
August 2023
Department of Cell and Molecular Biology, Biomedical Centre, Box 596, 751 24, Uppsala, Sweden.
tRNA genes are transcribed as precursors and RNase P generates the matured 5' end of tRNAs. It has been suggested that residue - 1 (the residue immediately 5' of the scissile bond) in the pre-tRNA interacts with the well-conserved bacterial RNase P RNA (RPR) residue A (Escherichia coli numbering). The way A interacts with residue - 1 is not clear.
View Article and Find Full Text PDFCells
July 2023
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia.
Human Fe(II)/α-ketoglutarate-dependent dioxygenase ABH2 plays a crucial role in the direct reversal repair of nonbulky alkyl lesions in DNA nucleobases, e.g., N-methyladenine (mA), N-methylcytosine (mC), and some etheno derivatives.
View Article and Find Full Text PDFJ Chromatogr A
August 2023
Synthetic Molecule Design and Development, Lilly Research Labs, Eli Lilly and Company, Indianapolis, IN 46285, United States. Electronic address:
The orthogonality of separation between ion-pair reversed phase (IP-RP), anion exchange (AEX), and hydrophilic interaction liquid chromatography (HILIC) was evaluated for oligonucleotides. A polythymidine standard ladder was first used to evaluate the three methods and showed zero orthogonality, where retention and selectivity were based on oligonucleotide charge/size under all three conditions. Next, a model 23-mer synthetic oligonucleotide containing 4 phosphorothioate bonds with 2' fluoro and 2'-O-methyl ribose modifications typical of small interfering RNA was used for evaluating orthogonality.
View Article and Find Full Text PDFNat Rev Mol Cell Biol
October 2023
State Key Laboratory of Protein and Plant Gene Research, School of Life Sciences, Peking University, Beijing, China.
Nucleobase modifications are prevalent in eukaryotic mRNA and their discovery has resulted in the emergence of epitranscriptomics as a research field. The most abundant internal (non-cap) mRNA modification is N-methyladenosine (mA), the study of which has revolutionized our understanding of post-transcriptional gene regulation. In addition, numerous other mRNA modifications are gaining great attention because of their major roles in RNA metabolism, immunity, development and disease.
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