Racemic Phospholipids for Origin of Life Studies
Open accessAbstract
Although prebiotic condensations of glycerol, phosphate and fatty acids produce phospholipid esters with a racemic backbone, most experimental studies on vesicles intended as protocell models have been carried out by employing commercial enantiopure phospholipids. Current experimental research on realistic protocell models urgently requires racemic phospholipids and efficient synthetic routes for their production. Here we propose three synthetic pathways starting from glycerol or from racemic solketal (α,β-isopropylidene-dl-glycerol) for the gram-scale production (up to 4 g) of racemic phospholipid ester precursors. We describe and compare these synthetic pathways with literature data. Racemic phosphatidylcholines and phosphatidylethanolamines were obtained in good yields and high purity from 1,2-diacylglycerols. Racemic POPC (rac-POPC, (R,S)-1-palmitoyl-2-oleoyl-3-phosphocholine), was used as a model compound for the preparation of giant vesicles (GVs). Confocal laser scanning fluorescence microscopy was used to compare GVs prepared from enantiopure (R)-POPC), racemic POPC (rac-POPC) and a scalemic mixture (scal-POPC) of (R)-POPC enriched with rac-POPC. Vesicle morphology and size distribution were similar among the different (R)-POPC, rac-POPC and scal-POPC, while calcein entrapments in (R)-POPC and in scal-POPC were significantly distinct by about 10%.
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The correlation between lipid rafts and membrane permeability is significant in the selection of stable functional polymers.
“A key investigation in OOL studies is the correlation between lipid rafts 1 (Edidin, 2003)and membrane permeability (Altamura et al., 2020; Eghiaian, 2015) that is significant in the selection of stable functional polymers.”
From The Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments (2023) · cites this paper as Altamura et al., 2020
The packaging of enantiopure phospholipids was plausibly more performant than that of racemic or scalemic ones.
“the packaging of enantiopure phospholipids was plausibly more performant than that of racemic or scalemic ones.”
From The Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments (2023) · cites this paper as Altamura et al., 2020
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- Authors
- Altamura, E., Comte, A., D’Onofrio, A., Roussillon, C., Fayolle, D., Buchet, R., Mavelli, F., Stano, P., Fiore, M., & Strazewski, P.
- Affiliations
- University of Bari Aldo Moro (IT)
- Lyon 1 Université (FR)
- University of Salento (IT)
- Corresponding author
- Fiore, Michele
- Strazewski, Peter
- ORCID
- Venue
- Symmetry
- Publisher
- MDPI AG
- Published
- 2020-07-03
- Volume
- 12
- Issue
- 7
- Pages
- 1108
- ISSN
- 2073-8994 (ISSN-L)
- OpenAlex
- W3039715355
- Cited by
- 23
- References
- 61
- Citations by year
- 2026: 1 · 2025: 2 · 2024: 4 · 2023: 4 · 2022: 7 · 2021: 2 · 2020: 3
- FWCI
- 1.78
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Symmetry (publishedVersion, cc-by)
- HAL (submittedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- AIRUS (submittedVersion, cc-by)
- CINECA IRIS Institutional Research Information System (University of Bari Aldo Moro) (submittedVersion)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Phosphorus compounds and reactions
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Lipid Membrane Structure and Behavior
- Keywords
- origin of life, phospholipid synthesis, solketal, phosphatidylcholine, phosphatidylethanolamine, POPC, giant vesicles, scalemic mixtures, vesicle morphology, prebiotic chemistry
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