Molecular-level insights into a tripolyphosphate and pyrophosphate templated membrane assembly

Prasad, Mahesh; Hazra, Bibhas; Sardar, Avijit; Mandal, Raki; Gayen, Soumajit; Tarafdar, Pradip K.

doi:10.1039/d3sm00017f

Cited by 3 publications

(5 citation statements)

References 86 publications

(117 reference statements)

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“…Similar experiments with OLEA-ADP suggest that it was less tolerable in the presence of Mg 2+ , and we found a clear solution at 4.0 mM Mg 2+ (Figure S16A). These experiments support the role of electrostatic and ionpair interactions 16,45 in forming vesicular assemblies. Thus, the number of phosphate units, the electrostatic and ion-pair interactions control the templated assembly of the protocellular membrane.…”

Section: Prebiotic Synthesis Of Ethanolamine-based Lipidssupporting

confidence: 69%

“…Similar to this, it may be possible that OLEA with a terminal positive charge (ammonium headgroup) and a shorter dodecyl chain might be assembled with ATP. Recently, we have shown the templated assembly of choline-based amphiphiles in the presence of tripolyphosphate . To investigate the ATP-templated assembly of ethanolamine-based lipids (OLEA), we mixed OLEA and ATP at various ratios in water.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we have shown the templated assembly of choline-based amphiphiles in the presence of tripolyphosphate. 45 To investigate the ATP-templated assembly of ethanolaminebased lipids (OLEA), we mixed OLEA and ATP at various ratios in water. The turbidity (scattering at 400 nm) of the 1.5 mM OLEA solution increased with the addition of ATP and reached a maximum at X ATP ≈ 0.25 (3:1 ratio of OLEA:ATP) (Figure 2A).…”

Section: Prebiotic Synthesis Of Ethanolamine-based Lipidsmentioning

confidence: 99%

“…However, the turbidity of OLEA-ADP was much lower (∼0.10) than that of OLEA-ATP (∼0. 45), suggesting that the number of phosphate units may control the aggregation. DLS measurements showed that the OLEA-ADP (2:1 ratio) aggregate was much smaller, ∼160 ± 30 nm (Figure 3C and Figure S12).…”

Section: Prebiotic Synthesis Of Ethanolamine-based Lipidsmentioning

confidence: 99%

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ATP-Assisted Protocellular Membrane Formation with Ethanolamine-Based Amphiphiles

et al. 2023

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Prebiotic membranes are one of the essential elements of the origin of life because they build compartments to keep genetic materials and metabolic machinery safe. Since modern cell membranes are made up of ethanolamine-based phospholipids, prebiotic membrane formation with ethanolamine-based amphiphiles and phosphates might act as a bridge between the prebiotic and contemporary eras. Here, we report the prebiotic synthesis of O-lauroyl ethanolamine (OLEA), O-lauroyl methyl ethanolamine (OLMEA), and O-lauroyl dimethylethanolamine (OLDMEA) under wet–dry cycles. Turbidimetric, NMR, DLS, fluorescence, microscopy, and glucose encapsulation studies highlighted that OLEA-ATP and OLMEA-ATP form protocellular membranes in a 3:1 ratio, where ATP acts as a template. OLDMEA with a dimethyl group did not form any membrane in the presence of ATP. ADP can also template OLEA to form vesicles in a 2:1 ratio, but the ADP-templated vesicles were smaller. This suggests the critical role of the phosphate backbone in controlling the curvature of supramolecular assembly. The mechanisms of hierarchical assembly and transient dissipative assembly are discussed based on templated-complex formation via electrostatic, hydrophobic, and H-bonding interactions. Our results suggest that N-methylethanolamine-based amphiphiles could be used to form prebiotic vesicles, but the superior H-bonding ability of the ethanolamine moiety likely provides an evolutionary advantage for stable protocell formation during the fluctuating environments of early earth.

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Section: Prebiotic Synthesis Of Ethanolamine-based Lipidssupporting

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: Prebiotic Synthesis Of Ethanolamine-based Lipidsmentioning

confidence: 99%

Section: Prebiotic Synthesis Of Ethanolamine-based Lipidsmentioning

confidence: 99%

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ATP-Assisted Protocellular Membrane Formation with Ethanolamine-Based Amphiphiles

et al. 2023

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“…Recently, our group proposed that apart from the anionic amphiphiles, cationic amphiphiles were also important in protocell formation and catalysis. − Particularly, we have shown that a lysine-based prebiotic cationic amphiphile and anionic fatty acids may work in tandem (catanionic complex formation) to form a prebiotic membrane at low CVC and assisted in regioselective peptide bond formation . The protocell forming ability of the mixture of cationic amino acid-based amphiphiles (lysine octyl ester, LysOct) and anionic fatty acid amphiphiles (decanoic acid) led to a window of opportunities to explore the capabilities of phosphate- and sulfate-based anionic amphiphiles.…”

Section: Introductionmentioning

confidence: 99%

Phosphate-Based Amphiphile and Lipidated Lysine Assemble into Superior Protocellular Membranes over Carboxylate and Sulfate-Based Systems: A Potential Missing Link between Prebiotic and the Modern Era?

Hazra,

Prasad,

Das

et al. 2023

Langmuir

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Self‐immolation Assisted Morphology Transformation of Prebiotic Lipidated‐cationic Amino Acids: Electro‐droplet Mediated C−C Coupling Reaction to Synthesize Macromolecules

Hazra,

Mandal,

Sahu

et al. 2024

Chemistry A European J

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Compartmentalization protected biomolecules from the fluctuating environments of early Earth. Although contemporary cells mostly use phospholipid‐based bilayer membranes, the utility of non‐bilayer compartments was not ruled out during the prebiotic and modern eras. In the present study, we demonstrated the prebiotic synthesis of lipidated cationic amino acid‐based amphiphiles (lauryl ester of lysine, Lys; ornithine, Orn; and 2,4‐diamino butyric acid, Dab) using model dry‐down reaction. Orn, and Dab‐based amphiphiles (OrnL and DabL) self‐assemble into micellar membranes but undergo pH‐responsive self‐immolation assisted transformation to lipid droplet‐like morphologies, a probable alternative compartment model in the prebiotic Earth. These cationic droplets encapsulated prebiotic molecules (isoprene) and assisted electron transfer reaction to synthesize isoprenoid derivatives at primitive Earth conditions. The self‐assembly of prebiotic amphiphiles, their transformation to droplet compartments, and droplet‐assisted C‐C bond formation reaction might help the evolution to synthesize various biomolecules required for the origin of life.

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Molecular-level insights into a tripolyphosphate and pyrophosphate templated membrane assembly

Abstract: Templated assembly of small molecules into nano-structural architectures has been used extensively by nature throughout its evolution. These systems were also studied in artificial systems to design phosphate templated assembly....

Cited by 3 publications

References 86 publications

ATP-Assisted Protocellular Membrane Formation with Ethanolamine-Based Amphiphiles

ATP-Assisted Protocellular Membrane Formation with Ethanolamine-Based Amphiphiles

Phosphate-Based Amphiphile and Lipidated Lysine Assemble into Superior Protocellular Membranes over Carboxylate and Sulfate-Based Systems: A Potential Missing Link between Prebiotic and the Modern Era?

Self‐immolation Assisted Morphology Transformation of Prebiotic Lipidated‐cationic Amino Acids: Electro‐droplet Mediated C−C Coupling Reaction to Synthesize Macromolecules

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