Crude phosphorylation mixtures containing racemic lipid amphiphiles self-assemble to give stable primitive compartments

Abstract : It is an open question how the chemical structure of prebiotic vesicle-forming amphiphiles complexified to produce robust primitive compartments that could safely host foreign molecules. Previous work suggests that comparingly labile vesicles composed of plausibly prebiotic fatty acids were eventually chemically transformed with glycerol and a suitable phosphate source into phospholipids that would form robust vesicles. Here we show that phosphatidic acid (PA) and phosphatidylethanolamine (PE) lipids can be obtained from racemic dioleoyl glycerol under plausibly prebiotic phosphorylation conditions. Upon in situ hydration of the crude phosphorylation mixtures only those that contained rac-DOPA (not rac-DOPE) generated stable giant vesicles that were capable of encapsulating water-soluble probes, as evidenced by confocal microscopy and flow cytometry. Chemical reaction side-products (identified by IR and MS and quantified by 1 H NMR) acted as co-surfactants and facilitated vesicle formation. To mimic the compositional variation of such primitive lipid mixtures, self-assembly of a combinatorial set of the above amphiphiles was tested, revealing that too high dioleoyl glycerol contents inhibited vesicle formation. We conclude that a decisive driving force for the gradual transition from unstable fatty acid vesicles to robust diacylglyceryl phosphate vesicles was to avoid the accumulation of unphosphorylated diacylglycerols in primitive vesicle membranes.
Document type :
Journal articles
Complete list of metadatas

Cited literature [73 references]  Display  Hide  Download

https://hal-udl.archives-ouvertes.fr/hal-02122490
Contributor : Umr5246 Icbms <>
Submitted on : Tuesday, May 7, 2019 - 1:51:06 PM
Last modification on : Wednesday, May 22, 2019 - 4:24:07 PM

File

s41598-017-18053-y.pdf
Publisher files allowed on an open archive

Identifiers

Citation

Dimitri Fayolle, Emiliano Altamura, Alice D'onofrio, Warren Madanamothoo, Bernard Fenet, et al.. Crude phosphorylation mixtures containing racemic lipid amphiphiles self-assemble to give stable primitive compartments. Scientific Reports, Nature Publishing Group, 2017, 7 (1), ⟨10.1038/s41598-017-18053-y⟩. ⟨hal-02122490⟩

Share

Metrics

Record views

17

Files downloads

34