Abiotic Regioselective Phosphorylation of Adenosine with Borate in Formamide
Abstract
Nearly 40 years ago, Schoffstall and his coworkers used formamide as a solvent to permit the phosphorylation of nucleosides by inorganic phosphate to give nucleoside phosphates, which (due to their thermodynamic instability with respect to hydrolysis) cannot be easily created in water by an analogous phosphorylation (the "water problem" in prebiotic chemistry). More recently, we showed that borate could stabilize certain carbohydrates against degradation (the "asphalt problem"). Here, we combine the two concepts to show that borate can work in formamide to guide the reactivity of nucleosides under conditions where they are phosphorylated. Specifically, reaction of adenosine in formamide with inorganic phosphate and pyrophosphate in the presence of borate gives adenosine-5'-phosphate as the only detectable phosphorylated product, with formylation (as opposed to hydrolysis) being the competing reaction.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Hydroxyapatite enhances the cross-aldol Lobry de Bruyn-Alberda-van Eckstein reaction using effective positioning of calcium ions on mineral surfaces, converting tetrose-2,4-diphosphate and hexose-2,4,6-triphosphate into ribose 5-phosphate.
“On the contrary, hydroxyapatite enhances the cross-aldol Lobry de Bruyn-Alberda-van Eckstein reaction using the effective positioning of calcium ions on the surface of the minerals (Furukawa et al., 2015; Larralde et al., 1995; Usami and Okamoto, 2017) thus tetrose-2-4-diphosphate and hexose-2-4-6-triposphate are converted in ribose 5-phosphate.”
From The Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments (2023) · cites this paper as Furukawa et al., 2015
Cites
Wilde, S. A., Valley, J. W., Peck, W. H., & Graham, C. M. (2001) · Nature · doi:10.1038/35051550 · Cited by 1,744 · see citing works
Synthesis of Purines under Possible Primitive Earth Conditions. I. Adenine from Hydrogen Cyanide
Oró, J., & Kimball, A. P. (1961) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(61)90033-9 · Cited by 406 · see citing works
Asphalt, Water, and the Prebiotic Synthesis of Ribose, Ribonucleosides, and RNA
Benner, S. A., Kim, H.-J., & Carrigan, M. A. (2012) · Accounts of Chemical Research · doi:10.1021/ar200332w · Cited by 281 · see citing works
Self-citationBiological Effects of High Ultraviolet Radiation on Early Earth—a Theoretical Evaluation
Cockell, C. S. (1998) · Journal of Theoretical Biology · doi:10.1006/jtbi.1998.0738 · Cited by 177 · see citing works
Selective Derivatization and Sequestration of Ribose from a Prebiotic Mix
Springsteen, G., & Joyce, G. F. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0483692 · Cited by 122 · see citing works
Hypothesis: Origin of life in deep-reaching tectonic faults
Schreiber, U., Locker-Grütjen, O., & Mayer, C. (2012) · Origins of Life and Evolution of Biospheres · doi:10.1007/s11084-012-9267-4 · Cited by 61 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Abiotic production of sugar phosphates and uridine ribonucleoside in aqueous microdroplets
Nam, I., Lee, J. K., Nam, H. G., & Zare, R. N. (2017) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1714896114 · Cited by 262 · see citing works
Deal, A. M., Rapf, R. J., & Vaida, V. (2021) · The Journal of Physical Chemistry A · doi:10.1021/acs.jpca.1c02864 · Cited by 105 · see citing works
Nucleobase and amino acid formation through impacts of meteorites on the early ocean
Furukawa, Y., Nakazawa, H., Sekine, T., Kobayashi, T., & Kakegawa, T. (2015) · Earth and Planetary Science Letters · doi:10.1016/j.epsl.2015.07.049 · Cited by 67 · see citing works
Self-citationEstimating the Capacity for Production of Formamide by Radioactive Minerals on the Prebiotic Earth
Adam, Z. R., Hongo, Y., Cleaves, H. J., Yi, R., Fahrenbach, A. C., Yoda, I., & Aono, M. (2018) · Scientific Reports · doi:10.1038/s41598-017-18483-8 · Cited by 52 · see citing works
The Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments
Chieffo, C., Shvetsova, A., Skorda, F., Lopez, A., & Fiore, M. (2023) · Astrobiology · doi:10.1089/ast.2023.0007 · Cited by 21 · see citing works
- Authors
- Furukawa, Y., Kim, H.-J., Hutter, D., & Benner, S. A.
- Affiliations
- Tohoku University (JP)
- Foundation for Applied Molecular Evolution (US)
- Corresponding author
- Furukawa, Yoshihiro
- Venue
- Astrobiology
- Publisher
- SAGE Publications
- Published
- 2015-04
- Volume
- 15
- Issue
- 4
- Pages
- 259-267
- ISSN
- 1531-1074 (ISSN-L)
- 1557-8070
- OpenAlex
- W1874455357
- Cited by
- 44
- References
- 6
- Citations by year
- 2026: 3 · 2025: 3 · 2024: 3 · 2023: 7 · 2022: 5 · 2021: 4 · 2020: 4 · 2019: 4 · 2018: 1 · 2017: 4 · 2016: 3 · 2015: 3
- FWCI
- 2.08
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Astrobiology (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Aeronautics and Space Administration
- Jet Propulsion Laboratory
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Organophosphorus compounds synthesis
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Keywords
- adenosine, borate, formamide, nucleoside phosphates, prebiotic chemistry, inorganic phosphate, pyrophosphate, nucleoside hydrolysis, formylation, regioselectivity, water problems
- MeSH terms
- Adenosine, Borates, Chromatography, High Pressure Liquid, Formamides, Phosphorylation, Stereoisomerism, Time Factors, Silicates, Proton Magnetic Resonance Spectroscopy
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
