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Cited by 91Origins and Evolution of LifeRNA and protein synthesis mechanismsLipid metabolism and biosynthesis

Length-Selective Synthesis of Acylglycerol-Phosphates through Energy-Dissipative Cycling

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Bonfio, Claudia, Caumes, Cécile, Duffy, Colm D., Patel, Bhavesh H., Percivalle, Claudia, Tsanakopoulou, Maria, Sutherland, John D.·2019·Journal of the American Chemical Society
DOI 10.1021/jacs.8b12331PMC PMC6506141
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Abstract

The main aim of origins of life research is to find a plausible sequence of transitions from prebiotic chemistry to nascent biology. In this context, understanding how and when phospholipid membranes appeared on early Earth is critical to elucidating the prebiotic pathways that led to the emergence of primitive cells. Here we show that exposing glycerol-2-phosphate to acylating agents leads to the formation of a library of acylglycerol-phosphates. Medium-chain acylglycerol-phosphates were found to self-assemble into vesicles stable across a wide range of conditions and capable of retaining mono- and oligonucleotides. Starting with a mixture of activated carboxylic acids of different lengths, iterative cycling of acylation and hydrolysis steps allowed for the selection of longer-chain acylglycerol-phosphates. Our results suggest that a selection pathway based on energy-dissipative cycling could have driven the selective synthesis of phospholipids on early Earth.

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Crossref · 10.1021/jacs.8b12331

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  • Several important classes of biomolecules, such as plausible prebiotic amino acids precursors, 2',3'-cyclic pyrimidine nucleotides, and glycerol phosphate, may have hydrogen cyanide and formaldehyde as common chemical precursors in the cyanosulfidic pathway.

    “They have shown that several important classes of biomolecules, such as plausible prebiotic amino acids precursors (Piotto et al., 2019), 2',3'-cyclic pyrimidine nucleotides, and glycerol phosphate, may have hydrogen cyanide ( 1 ) and formaldehyde as common chemical precursors in the aforementioned 'cyanosulfidic' pathway.”

    From The Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments (2023) · cites this paper as Bonfio et al., 2019

    In Results and Discussion, under “Non-enzymatic Acylation of Glycerol-Phosphates” (page unavailable), the paper reports synthesis of glycerol-phosphates from glyceraldehyde and identifies glyceraldehyde as a product of cyanosulfidic chemistry. It does not establish hydrogen cyanide and formaldehyde as common precursors of the listed biomolecule classes, or report the claimed pathway to 2′,3′-cyclic pyrimidine nucleotides. The amino-acid-precursor phrase carries a separate citation to Piotto et al. (LLM, conf=0.84)

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  • Glyceraldehyde is an important precursor in the formose reaction and in the synthesis of glycerine, a lipid precursor, through an isomerization step followed by reduction with SH2.

    “One of these aldehydes, glyceraldehyde, is an important precursor not only in the formose reaction but also in the synthesis of glycerine (14), a lipid precursor,102 for instance through an isomerization step followed by reduction with SH2”

    From The protometabolic nature of prebiotic chemistry (2023) · cites this paper as [102]

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Research works printed but not linked: 27

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Authors
Bonfio, C., Caumes, C., Duffy, C. D., Patel, B. H., Percivalle, C., Tsanakopoulou, M., & Sutherland, J. D.
Affiliations
  • MRC Laboratory of Molecular Biology (GB)
  • Medical Research Council Laboratory of Molecular Biology , Cambridge Biomedical Campus, Francis Crick Avenue , ,
Corresponding author
Sutherland, John D.
ORCID
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2019-02-15
Volume
141
Issue
9
Pages
3934-3939
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/jacs.8b12331
PMC
PMC6506141
OpenAlex
W2914851181
Cited by
91
References
11
Citations by year
2026: 11 · 2025: 11 · 2024: 10 · 2023: 18 · 2022: 11 · 2021: 14 · 2020: 9 · 2019: 7
FWCI
5.47
Type
journal article
Language
en
Open access
Licence
Locations
  • Journal of the American Chemical Society (publishedVersion, cc-by)
  • PubMed Central (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • Simons Foundation (290362)
  • Medical Research Council (MC_UP_A024_1009)
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
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Lipid metabolism and biosynthesis
Keywords
phospholipid self-assembly, vesicle formation, origin of life, prebiotic chemistry, glycerol-2-phosphate, acylation, hydrolysis, early Earth

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