Adenine Synthesis in Interstellar Space: Mechanisms of Prebiotic Pyrimidine-Ring Formation of Monocyclic HCN-Pentamers

Glaser, Rainer; Hodgen, Brian; Farrelly, Dean; McKee, Elliot

doi:10.1089/ast.2006.0112

Cited by 83Origins and Evolution of LifeAstrophysics and Star Formation StudiesSpace Science and Extraterrestrial Life

Adenine Synthesis in Interstellar Space: Mechanisms of Prebiotic Pyrimidine-Ring Formation of Monocyclic HCN-Pentamers

Glaser, Rainer, Hodgen, Brian, Farrelly, Dean, McKee, Elliot·2007·Astrobiology

DOI 10.1089/ast.2006.0112

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Abstract

The question whether the nucleobases can be synthesized in interstellar space is of fundamental significance in considerations of the origin of life. Adenine is formally the HCN pentamer, and experiments have demonstrated that adenine is formed under certain conditions by HCN pentamerization in gas, liquid, and condensed phases. Most mechanistic proposals invoke the intermediacy of the HCN tetramer AICN (4), and it is thought that adenine synthesis is completed by addition of the 5(th) HCN to 4 to form amidine 5 and subsequent pyrimidine cyclization. In this context, we have been studying the mechanism for prebiotic pyrimidine-ring formation of monocyclic HCN-pentamers with ab initio electronic structure theory. The calculations model gas phase chemistry, and the results primarily inform discussions of adenine synthesis in interstellar space. Purine formation requires tautomerization of 5 to the conjugated amidine 6 (via hydrogen-tunneling, thermally with H(+) -catalysis, or by photolysis) or to keteneimine 7 (by photolysis). It was found that 5-(N'-formamidinyl)-1H-imidazole-4-carbonitrile (6) can serve as a substrate for proton-catalyzed purine formation under photolytic conditions and N-(4-(iminomethylene)-1H-imidazol-5(4H)-ylidene)formamidine (7) can serve as a substrate for uncatalyzed purine formation under photolytic conditions. The absence of any sizeable activation barrier for the cyclization of 7 to the (Z)-imino form of 9H-adenine (Z)-2 is quite remarkable, and it is this feature that allows for the formation of the purine skeleton from 7 without any further activation.

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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 [126]

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Authors: Glaser, R., Hodgen, B., Farrelly, D., & McKee, E.
Affiliations: University of Missouri (US)
Creighton University (US)
University of Manchester (GB)
Saint Louis University (US)
ORCID: Glaser, Rainer
Venue: Astrobiology
Publisher: SAGE Publications
Published: 2007-06
Volume: 7
Issue: 3
Pages: 455-470
ISSN: 1531-1074 (ISSN-L)
1557-8070
DOI: 10.1089/ast.2006.0112
OpenAlex: W1997881544
Cited by: 83
References: 55
Citations by year: 2026: 4 · 2025: 1 · 2024: 1 · 2023: 11 · 2022: 4 · 2021: 3 · 2020: 7 · 2019: 2 · 2018: 4 · 2017: 6 · 2016: 6 · 2015: 5 · 2014: 3 · 2013: 2 · 2012: 6
FWCI: 2.99
Type: journal article
Language: en
Open access: closed
Locations: Astrobiology (publishedVersion)
PubMed (publishedVersion)
Funders: National Aeronautics and Space Administration
National Institute of General Medical Sciences (R01GM061027, GM61027)
Topics: Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Astrophysics and Star Formation Studies
Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Space Science and Extraterrestrial Life
Keywords: adenine synthesis, interstellar medium, prebiotic chemistry, proton catalysis, hydrogen tunneling, photolysis, origin of life, gas-phase reactions
MeSH terms: Origin of Life, Adenine, Extraterrestrial Environment, Models, Chemical, Protons, Thermodynamics, Exobiology

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Adenine Synthesis in Interstellar Space: Mechanisms of Prebiotic Pyrimidine-Ring Formation of Monocyclic HCN-Pentamers

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