An Investigation of Prebiotic Purine Synthesis from the Hydrolysis of HCN Polymers
Abstract
The polymerization of concentrated NH4CN solutions has been studied at various temperatures and ammonia concentrations. The products of the oligomerization of ammonium cyanide include adenine and guanine, as well as trace amounts of 2,6-diaminopurine. Our results indicate that the adenine yield is not strongly dependent on temperature. Guanine is produced in lower yield. The original studies by Oró and Kimball (1961) showed that the 6 N HCl hydrolysis of the NH4CN polymerization supernatant greatly increased the adenine yield. However, this hydrolysis also decomposes adenine and other purines. Therefore, we have measured the yields from an NH4CN polymerization as a function of hydrolysis time, and found that shorter hydrolytic periods give higher yields of adenine. We have also investigated the hydrolysis of the supernatant at pH 8, which is a more reasonable model of primitive oceanic conditions, and found that the adenine yield is comparable to that obtained with acid hydrolysis (approximately 0.1%). The yield of adenine does not decline at longer hydrolysis times because of the greater stability of adenine at pH 8. The insoluble black polymer formed from NH4CN has been analyzed by both acid and neutral hydrolysis. In both cases adenine yields of approximately 0.05% were obtained. This suggests that the polymer may have been as important a prebiotic source of purines as the usually analyzed supernatant.
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Hydrogen cyanide oligomers may have played a significant role in the synthesis of a wide range of prebiotic molecules.
“For example, hydrogen cyanide (HCN) oligomers may have played a significant role in the synthesis of a wide range of prebiotic molecules [122-126], and recently, dimeric forms of HCN (cyanomethanimine) [127] have been detected in the interstellar medium.”
From The future of quantum biology (2018) · cites this paper as [125]
Cites
Synthesis of adenine from ammonium cyanide
Oro, J. A. (1960) · Biochemical and Biophysical Research Communications · doi:10.1016/0006-291x(60)90138-8 · Cited by 482 · 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
The stability of the RNA bases: implications for the origin of life
Levy, M., & Miller, S. L. (1998) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.95.14.7933 · Cited by 297 · see citing works
Self-citationHCN: A plausible source of purines, pyrimidines and amino acids on the primitive earth
Ferris, J. P., Joshi, P. C., Edelson, E. H., & Lawless, J. (1978) · Journal of Molecular Evolution · doi:10.1007/bf01733839 · Cited by 287 · see citing works
Mechanism of ε15 conversion studied with bacteriophage mutants
Bray, D., & Robbins, P. W. (1967) · Journal of Molecular Biology · doi:10.1016/s0022-2836(67)80037-8 · Cited by 280 · see citing works
Studies in prebiotic synthesis
Fuller, W. D., Sanchez, R. A., & Orgel, L. E. (1972) · Journal of Molecular Biology · doi:10.1016/0022-2836(72)90383-x · Cited by 280 · see citing works
Kimball (1962) · doi:10.1016/0003-9861(62)90412-5 · Cited by 230 · see citing works
Saladino, R. (2001) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(00)00340-0 · Cited by 208 · see citing works
Conditions for Purine Synthesis: Did Prebiotic Synthesis Occur at Low Temperatures?
Sanchez, R. A., Ferris, J. P., & Orgel, L. E. (1966) · Science · doi:10.1126/science.153.3731.72 · Cited by 203 · see citing works
An Unusual Photochemical Rearrangement in the Synthesis of Adenine from Hydrogen Cyanide1
Ferris, J. P., & Orgel, L. E. (1966) · Journal of the American Chemical Society · doi:10.1021/ja00957a050 · Cited by 160 · see citing works
Prebiotic Synthesis of Adenine and Amino Acids Under Europa-like Conditions
Levy, M. (2000) · Icarus · doi:10.1006/icar.2000.6365 · Cited by 149 · see citing works
Impact melting of frozen oceans on the early Earth: Implications for the origin of life
Bada, J. L., Bigham, C., & Miller, S. L. (1994) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.91.4.1248 · Cited by 146 · see citing works
Self-citationThe prebiotic role of adenine: A critical analysis
Shapiro, R. (1995) · Origins of Life and Evolution of Biospheres · doi:10.1007/bf01581575 · Cited by 134 · see citing works
Studies in prebiotic synthesis
Sanchez, R. A., Ferris, J. P., & Orgel, L. E. (1968) · Journal of Molecular Biology · doi:10.1016/0022-2836(68)90132-0 · Cited by 110 · see citing works
Frick, L., Neela, J. P. M., & Wolfenden, R. V. (1987) · Bioorganic Chemistry · doi:10.1016/0045-2068(87)90011-3 · Cited by 90 · see citing works
Schwartz, A. W., & Goverde, M. (1982) · Journal of Molecular Evolution · doi:10.1007/bf01733902 · Cited by 82 · see citing works
Production of Guanine from NH4CN Polymerizations
Levy, M., Miller, S. L., & Oro, J. F. (1999) · Journal of Molecular Evolution · doi:10.1007/pl00006539 · Cited by 79 · see citing works
Self-citationPrebiotic adenine synthesis from HCN—Evidence for a newly discovered major pathway
Voet, A. B., & Schwartz, A. W. (1983) · Bioorganic Chemistry · doi:10.1016/0045-2068(83)90003-2 · Cited by 69 · see citing works
Ferris, J. P., Donner, D. B., & Lobo, A. P. (1973) · Journal of Molecular Biology · doi:10.1016/0022-2836(73)90042-9 · Cited by 48 · see citing works
Recent progress in the prebiotic chemistry of HCN
Schwartz, A. W., Voet, A. B., & Veen, M. (1984) · Origins of Life and Evolution of Biospheres · doi:10.1007/bf00933644 · Cited by 43 · see citing works
Aqueous solubilities and enthalpies of solution of adenine and guanine
DeVoe, H., & Wasik, S. P. (1984) · Journal of Solution Chemistry · doi:10.1007/bf00648591 · Cited by 36 · see citing works
Synthesis of Adenine from HCN Tetramer and Ammonium Formate
Hill, A. R., & Orgel, L. E. (2002) · Origins of Life and Evolution of Biospheres · doi:10.1023/a:1016070723772 · Cited by 36 · see citing works
Schwartz, A. W. (1998) · Cambridge University Press eBooks · doi:10.1017/cbo9780511626180.013 · Cited by 26 · see citing works
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- Authors
- Borquez, E., Cleaves, H. J., Lazcano, A., & Miller, S. L.
- Affiliations
- University of California San Diego (US)
- Universidad Nacional Autónoma de México (MX)
- Corresponding author
- Lazcano, Antonio
- Venue
- Origins of Life and Evolution of Biospheres
- Published
- 2005-04
- Volume
- 35
- Issue
- 2
- Pages
- 79-90
- ISSN
- 0169-6149 (ISSN-L)
- 1573-0875
- OpenAlex
- W2156708978
- Cited by
- 80
- References
- 23
- Citations by year
- 2026: 3 · 2025: 4 · 2024: 1 · 2023: 3 · 2022: 3 · 2021: 5 · 2020: 5 · 2019: 4 · 2018: 5 · 2017: 4 · 2016: 4 · 2015: 3 · 2014: 4 · 2013: 7 · 2012: 4
- FWCI
- 1.55
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Origins of Life and Evolution of Biospheres (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Aeronautics and Space Administration
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Space Science and Extraterrestrial Life
- Keywords
- adenine, guanine, 2,6-diaminopurine, hydrolysis, origin of life
- MeSH terms
- Origin of Life, Adenine, Cyanides, Guanine, Hydrogen Cyanide, Hydrolysis, Polymers, Evolution, Chemical
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