ArticleAngewandte Chemie (International ed. in English)2020
The Enzyme-Free Release of Nucleotides from Phosphoramidates Depends Strongly on the Amino Acid.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Yield and fidelity of early steps of ribosome-free translation depend on the RNA anchoring.Nucleic acids research · 2026Article
- The Role of Chemistry Across Disciplines From Humanities to Life Sciences in Understanding Complexity and Emergence.Angewandte Chemie (International ed. in English) · 2026Review
- Article
- The protometabolic nature of prebiotic chemistry.Chemical Society reviews · 2023Review
- Conserved Characteristics of NMPylation Activities of Alpha- and Betacoronavirus NiRAN Domains.Journal of virology · 2023Article
- Prodrugs of Nucleoside 5'-Monophosphate Analogues: Overview of the Recent Literature Concerning their Synthesis and Applications.Current medicinal chemistry · 2023Review
- A Ribonucleotide ↔ Phosphoramidate Reaction Network Optimized by Computer-Aided Design.Journal of the American Chemical Society · 2022Article
- Carbodiimide-Driven Dimerization and Self-Assembly of Artificial, Ribose-Based Amphiphiles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Determining the Diastereoselectivity of the Formation of Dipeptidonucleotides by NMR Spectroscopy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Single nucleotide translation without ribosomes.Nature chemistry · 2021Article
- Co-crystallization of an organic solid and a tetraaryladamantane at room temperature.Beilstein journal of organic chemistry · 2021Article
- The Enzyme-Free Release of Nucleotides from Phosphoramidates Depends Strongly on the Amino Acid.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
5 authors.
Funding
Abstract
Phosphoramidates composed of an amino acid and a nucleotide analogue are critical metabolites of prodrugs, such as remdesivir. Hydrolysis of the phosphoramidate liberates the nucleotide, which can then be phosphorylated to become the pharmacologically active triphosphate. Enzymatic hydrolysis has been demonstrated, but a spontaneous chemical process may also occur. We measured the rate of enzyme-free hydrolysis for 17 phosphoramidates of ribonucleotides with amino acids or related compounds at pH 7.5. Phosphoramidates of proline hydrolyzed fast, with a half-life time as short as 2.4 h for Pro-AMP in ethylimidazole-containing buffer at 37 °C; 45-fold faster than Ala-AMP and 120-fold faster than Phe-AMP. Crystal structures of Gly-AMP, Pro-AMP, βPro-AMP and Phe-AMP bound to RNase A as crystallization chaperone showed how well the carboxylate is poised to attack the phosphoramidate, helping to explain this reactivity. Our results are significant for the design of new antiviral prodrugs.
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