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Cited by 122Origins and Evolution of LifeRNA and protein synthesis mechanismsSpace Science and Extraterrestrial Life

L-amino acids catalyze the formation of an excess of D-glyceraldehyde, and thus of other D sugars, under credible prebiotic conditions

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Breslow, Ronald, Cheng, Zhan-Ling·2010·Proceedings of the National Academy of Sciences
DOI 10.1073/pnas.1001639107PMC PMC2851924
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Abstract

Previous work by us, and others, has shown that the formation of amino acids on prebiotic earth with the geometric arrangement called the L configuration can be understood. Some meteorites of the carbonaceous chondritic type deliver unusual amino acids, with alpha-methyl groups, which have an excess of the L isomers. We previously showed that in decarboxylative transamination reactions under credible prebiotic conditions they produce normal amino acids that also have a preference for the L isomer, as is found in our proteins. We, and others, showed that as little as a 1% excess of the L isomers could be amplified up to a 95/5 ratio of L over D on simple evaporation of a solution, so life could start with such a solution in which the dominant L isomers would be selectively chosen. We now find that the geometry of sugars referred to D, as in D-ribose or D-glucose, is not an independent mystery. D-glyceraldehyde, the simplest sugar with a D center, is the basic unit on which other sugars are built. We find that the synthesis of glyceraldehyde by reaction of formaldehyde with glycolaldehyde is catalyzed under prebiotic conditions to D/L ratios greater than 1, to as much as 60/40, by a representative group of L-amino acids (with the exception of L-proline). The D/L glyceraldehyde ratio in water solution is amplified to 92/8 using simple selective solubilities of the D and the DL forms. This D center would then be carried into the prebiotic syntheses of larger sugars.

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  • All (S)-amino acids except (S)-proline provided glyceraldehyde with a predominant R configuration, up to 20% e.e. with (S)-glutamic acid.

    “It was found that all (S)-amino acids, except (S)-proline, provided glyceraldehyde with a predominant R configuration (up to 20% e.e. with (S)-glutamic acid, Fig. 20, ( 2)).65,510”

    From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [510]

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Authors
Breslow, R., & Cheng, Z.-L.
Affiliations
Columbia University (US)
Corresponding author
Breslow, Ronald
Venue
Proceedings of the National Academy of Sciences
Publisher
National Academy of Sciences
Published
2010-03-15
Volume
107
Issue
13
Pages
5723-5725
ISSN
  • 0027-8424 (ISSN-L)
  • 1091-6490
DOI
10.1073/pnas.1001639107
PMC
PMC2851924
OpenAlex
W2068666654
Cited by
122
References
3
Citations by year
2026: 4 · 2025: 5 · 2024: 6 · 2023: 8 · 2022: 10 · 2021: 9 · 2020: 10 · 2019: 8 · 2018: 2 · 2017: 11 · 2016: 7 · 2015: 9 · 2014: 2 · 2013: 6 · 2012: 7
FWCI
5.54
Type
journal article
Language
en
Open access
Locations
  • Proceedings of the National Academy of Sciences (publishedVersion)
  • PubMed Central (publishedVersion)
  • PubMed (publishedVersion)
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
L-amino acids, D-glyceraldehyde, prebiotic chemistry, origin of homochirality, formaldehyde, glycolaldehyde, carbonaceous chondrites, α-methyl amino acids, sugar synthesis, D-sugars
MeSH terms
Origin of Life, Amino Acids, Carbohydrates, Catalysis, Glyceraldehyde, Models, Chemical, Stereoisomerism, Molecular Structure, Meteoroids, Evolution, Chemical

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