On the origin of terrestrial homochirality for nucleosides and amino acids
Open accessAbstract
Before life could start on earth, it was important that the amino acid building blocks be present in a predominant handedness called the L configuration and that the ribose of RNA be predominantly in the D configuration. Because ordinary chemical processes would produce them in equal L and D amounts, it has long been a puzzle how the needed selectivities could have arisen. Carbonaceous chondrites such as the Murchison meteorite, which landed in Australia in 1969, brought some unusual amino acids with a methyl group replacing their α hydrogen. They cannot racemize and have a small but real excess of those with the L configuration. We have shown that they can partake in a synthesis of normal L amino acids under credible prebiotic conditions. We and others showed that small preferences can be amplified into solutions with very high dominance of the L amino acids because of the higher solubility of the pure L form than of the more stable DL racemic compound crystal. Here, we show that such solubility-based amplification of small excesses of three D nucleosides, uridine, adenosine, and cytidine, can also occur to form solutions with very high D dominance under credible prebiotic conditions. Guanosine crystallizes as a conglomerate and does not amplify in this way. However, under prebiotic conditions it could have been formed from homochiral D ribose from the hydrolysis of amplified adenosine or cytidine.
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Valine shows a eutectic of 47% ee, meaning a much lower level of chiral amplification is possible for this amino acid.
“Valine, on the other hand, shows a eutectic of 47% ee, which means that a much lower level of chiral ampli fi cation is possible for this amino acid.”
From The Origin of Biological Homochirality (2019) · cites this paper as Breslow and Cheng 2009
Serine shows a eutectic of 99% ee, meaning a nearly homochiral solution is achievable even when the overall ee of solid and solution combined is close to racemic.
“The proteinogenic amino acid serine shows a eutectic of 99% ee, meaning that a nearly homochiral solution is achievable even when the overall ee of the solid and solution combined is close to racemic.”
From The Origin of Biological Homochirality (2019) · cites this paper as Breslow and Cheng 2009
Cites
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“(11) have reported a more extensive studies, with similar results for the cases we examined, by simply suspending the mixtures in small amounts of water (9, 11).”
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Levine, M., Kenesky, C. S., Mazori, D., & Breslow, R. (2008) · Organic Letters · doi:10.1021/ol8007099 · Cited by 54 · see citing works
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Prebiotic Systems Chemistry: New Perspectives for the Origins of Life
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Chiral Sugars Drive Enantioenrichment in Prebiotic Amino Acid Synthesis
Wagner, A. J., Zubarev, D. Y., Aspuru-Guzik, A., & Blackmond, D. G. (2017) · ACS Central Science · doi:10.1021/acscentsci.7b00085 · Cited by 52 · see citing works
A likely possible origin of homochirality in amino acids and sugars on prebiotic earth
Breslow, R. (2011) · Tetrahedron Letters · doi:10.1016/j.tetlet.2010.08.094 · Cited by 35 · see citing works
Self-citation
- Authors
- Breslow, R., & Cheng, Z.-L.
- Affiliations
- Columbia University (US)
- Venue
- Proceedings of the National Academy of Sciences
- Publisher
- National Academy of Sciences
- Published
- 2009-06-09
- Volume
- 106
- Issue
- 23
- Pages
- 9144-9146
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- PMC
- PMC2695116
- OpenAlex
- W1995357477
- Cited by
- 118
- References
- 3
- Citations by year
- 2026: 2 · 2025: 4 · 2024: 3 · 2023: 7 · 2022: 7 · 2021: 15 · 2020: 3 · 2019: 11 · 2018: 5 · 2017: 3 · 2016: 3 · 2015: 4 · 2014: 6 · 2013: 4 · 2012: 6
- FWCI
- 6.89
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Proceedings of the National Academy of Sciences (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Science Foundation
- 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
- homochirality, origin of life, prebiotic chemistry, Murchison meteorite, amino acid enantiomers, nucleosides, uridine, adenosine, cytidine, guanosine, racemization, D-ribose, L-amino acids, carbonaceous chondrites
- MeSH terms
- Amino Acids, Australia, Nucleosides, Ribose, Solubility, Stereoisomerism, Meteoroids, Evolution, Chemical
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