Cyclophospholipids Increase Protocellular Stability to Metal Ions

Toparlak, Ö. Duhan; Karki, Megha; Ortuno, Veronica Egas; Krishnamurthy, Ramanarayanan; Mansy, Sheref S.

doi:10.1002/smll.201903381

Cited by 39 publications

(44 citation statements)

References 47 publications

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“…In addition, prior work on an RNA aptamer found that encapsulation in fatty acid vesicles and POPC vesicles gave similar effects on RNA activity ( 34 ). Exploration of different vesicle compositions mimicking protocells, such as cyclic phospholipids ( 77 ), might be an avenue of future interest.…”

Section: Discussionmentioning

confidence: 99%

Encapsulation of ribozymes inside model protocells leads to faster evolutionary adaptation

Lai

Liu

Chen

2021

Proc. Natl. Acad. Sci. U.S.A.

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Functional biomolecules, such as RNA, encapsulated inside a protocellular membrane are believed to have comprised a very early, critical stage in the evolution of life, since membrane vesicles allow selective permeability and create a unit of selection enabling cooperative phenotypes. The biophysical environment inside a protocell would differ fundamentally from bulk solution due to the microscopic confinement. However, the effect of the encapsulated environment on ribozyme evolution has not been previously studied experimentally. Here, we examine the effect of encapsulation inside model protocells on the self-aminoacylation activity of tens of thousands of RNA sequences using a high-throughput sequencing assay. We find that encapsulation of these ribozymes generally increases their activity, giving encapsulated sequences an advantage over nonencapsulated sequences in an amphiphile-rich environment. In addition, highly active ribozymes benefit disproportionately more from encapsulation. The asymmetry in fitness gain broadens the distribution of fitness in the system. Consistent with Fisher’s fundamental theorem of natural selection, encapsulation therefore leads to faster adaptation when the RNAs are encapsulated inside a protocell during in vitro selection. Thus, protocells would not only provide a compartmentalization function but also promote activity and evolutionary adaptation during the origin of life.

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Section: Discussionmentioning

confidence: 99%

Encapsulation of ribozymes inside model protocells leads to faster evolutionary adaptation

Lai

Liu

Chen

2021

Proc. Natl. Acad. Sci. U.S.A.

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“…Alternatively, G3P can be produced from glycerol and is catalysed by a glycerol kinase (GK) in bacteria and eukarya, while archaea lacks GK. [21,65] To the best of our knowledge, there is no GK producing G1P. So far, the catalytic activity of one and the same enzyme producing both G1P and G3P from glycerol, if it existed, was not retained during the evolution.…”

Section: Scheme 3 Biosynthetic Pathways Leading To G3p (A) and G1p (mentioning

confidence: 99%

“…Several plausible prebiotic synthesis were explored, however all the proposed pathways, carried out in enzyme free conditions from glycerol (3) yield racemic phospholipids (6−8, Scheme 2-A) [50,52,[55][56][57][58][59] or racemic mixtures of glycerol phosphates (5a−c and 9−10, Scheme 2-B [34,[60][61][62][63][64]. In addition, the chemical imbalance between the R:S ratio of mono-and di-alky phosphates (6, 12 scheme 2-C) and cyclic glycerophosphates (cGP, 13, scheme 2-D) [65,66] from di-acyl glycerols 12 or glycerol 3, respectively, were not reported or investigated either. Remarkably, all the phospholipids crude mixtures containing 6−8, 12 and 13 are able, using appropriate buffers, to form giant vesicles that per sizes and membranes properties are similar to that of lipid bilayer of modern cells.…”

Section: Racemic Amphiphiles and Their Precursorsmentioning

confidence: 99%

Symmetry Breaking of Phospholipids

Buchet¹,

Fiore²

2020

Preprint

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Either stereo reactants or stereo catalysis from achiral or chiral molecules are prerequisite to obtain pure enantiomeric lipid derivatives. We reviewed a few plausible organic syntheses of phospholipids under prebiotic conditions with a special attention to the starting materials as pro-chiral dihydroxyacetone and dihydroxyacetone phosphate (DHAP), which are the key molecules to break symmetry in phospholipids. The advantages of homochiral membranes compared to those of heterochiral membranes were analysed in term of specific recognition, optimal functions of enzymes, membrane fluidity and topological packing. All biological membranes contain enantiomeric lipids in modern bacteria, eukarya and archaea. The contemporary archaea, comprising of methanogens, halobacteria and thermoacidophiles are living under extreme conditions reminiscent of primitive environment and may indicate the origin of one ancient evolution path of lipid biosynthesis. The analysis of lipid metabolism reveals that all modern cells including archaea synthetize enantiomeric lipid precursors from prochiral DHAP. sn-glycerol-1-phosphate dehydrogenase (G1PDH), usually found in archaea, catalyses the formation of sn-glycerol-1-phosphate (G1P), while sn-glycerol-3-phosphate dehydrogenase (G3PDH) catalyses the formation of sn-glycerol-3-phosphate (G3P) in bacteria and eukarya. The selective enzymatic activity seems to be the main strategy that evolution retained to obtain enantiomeric pure lipids. The occurrence of two genes encoding for G1PDH and G3PDH, served to build up an evolution tree and the basis of our review focusing on the evolution of these two genes. Gene encoding for G3PDH in Eukarya may originate from G3PDH gene found in rare archaea indicating that archaea appeared earlier in the evolution tree than eukarya. Archaea and bacteria evolved probably separately, due to their distinct respective genes coding for G1PDH and G3PDH. The suggested hypothesis is that catalysis of homochiral G1P or G3P from DHAP are more efficient than those leading to racemic G1P and G3P, since there are no enzymes able to synthesize racemic G1P and G3P from DHAP. We propose that G1PDH or G3DPH, which are not “image mirror enzymes” but belonging to distinct family of proteins, emerged separately during evolution. They were probably selected for their efficient catalytic activities during evolution from large libraries of vesicles containing various biopolymers, including amino acids, carbohydrates, nucleic acids, lipids, and meteorite components to induce chemical imbalance.

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“…Later, Duhan et al. in 2019 showed that indeed these cyclophospholipids increase the stability of fatty acid protocells [25] . Thus, phosphorylation by DAP of the three different classes of molecules, nucleosides, amino acids, and glycerol/fatty acids ‐under similar ambient conditions‐ led to their corresponding higher‐order structures, oligonucleotides, peptides, and protocells, respectively.…”

Section: Dap: Reactions With Organic Substratesmentioning

confidence: 99%

Diamidophosphate (DAP): A Plausible Prebiotic Phosphorylating Reagent with a Chem to BioChem Potential?

Osumah

Krishnamurthy

2021

ChemBioChem

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Known since the 1890s, diamidophosphate (DAP) has been investigated within the context of its inorganic chemistry. In 1999 – with the demonstration of DAP's potential as a phosphorylating agent of sugars in aqueous medium – began the exciting phase of research about DAP's role as a plausible prebiotic phosphorylating agent. More recently, in the last five years, there has been a steady increase in the publications that have documented the surprising versatility of DAP enabling the emergence of many classes of biomolecules of life, such as nucleic acids, peptides and protocells. Thus, though in its infancy, DAP seems to be uniquely positioned to play a central role in modelling abiotic‐ to prebiotic‐chemical evolution. In this context, there is a need for systematic investigations for: (a) establishing DAP's likely availability on the early Earth, and (b) developing DAP's potential as a tool for use in synthetic and bioorganic chemistry.

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Cyclophospholipids Increase Protocellular Stability to Metal Ions

Cited by 39 publications

References 47 publications

Encapsulation of ribozymes inside model protocells leads to faster evolutionary adaptation

Encapsulation of ribozymes inside model protocells leads to faster evolutionary adaptation

Symmetry Breaking of Phospholipids

Diamidophosphate (DAP): A Plausible Prebiotic Phosphorylating Reagent with a Chem to BioChem Potential?

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