Abiogenic Syntheses of Lipoamino Acids and Lipopeptides and their Prebiotic Significance

Sproul, Gordon

doi:10.1007/s11084-015-9451-4

Cited by 9 publications

(9 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…They can be considered as a bridge between the lipid world and the peptide world, having structural features of both lipids and amino acids (and even peptides). They could get synthesized from fatty acids and non-activated amino acids under prebiotically pertinent conditions, 63 and cationic NAAs have also been shown to facilitate membrane–RNA interactions. 54 These studies highlight the plausible availability and functional significance of NAAs in a prebiotic era.…”

Section: Discussionmentioning

confidence: 99%

Spontaneous emergence of membrane-forming protoamphiphiles from a lipid–amino acid mixture under wet–dry cycles

2021

View full text Add to dashboard Cite

show abstract

Section: Discussionmentioning

confidence: 99%

Spontaneous emergence of membrane-forming protoamphiphiles from a lipid–amino acid mixture under wet–dry cycles

2021

View full text Add to dashboard Cite

show abstract

“…They can be considered as a bridge between the lipid world and the peptide world, having structural features of both lipids and amino acids (and even peptides). They could get synthesized from fatty acids and nonactivated amino acids under prebiotically pertinent conditions 57 , and cationic NAAs have also been shown to facilitate membrane-RNA interactions 46 . These studies highlight the plausible availability and functional significance of NAAs in a prebiotic era.…”

Section: Discussionmentioning

confidence: 99%

Spontaneous Emergence of Membrane-Forming Protoamphiphiles from a Lipid-Amino Acid Mixture Under Wet-Dry Cycles

Joshi

Sawant

Rajamani

2020

Preprint

View full text Add to dashboard Cite

The prelude to the origin of cellular life on Earth would have involved a fundamental step, that of protocell formation. This involves the coming together of two crucial processes; abiotic synthesis of informational and catalytic polymers, and the assembly of membrane compartments. Mutual interactions between these processes would have likely affected the emergence and early stages of protocell evolution. Previous investigations have predominantly focused on cooperative interactions, often neglecting any competitive behavior that might ensue as ‘counterproductive cross-talk’. However, in a realistic scenario, both cooperative and competitive reactions would have occurred simultaneously in a complex prebiotic soup, generating a plethora of chemical species with their own prebiotic implications. In this study, we followed a systematic and unbiased approach to explore this interdependence. We used a lipid-amino acid system to demonstrate the above-mentioned phenomenon wherein we investigated the effect of a membrane-forming amphiphile on peptide synthesis, under prebiotically plausible conditions. Interestingly, our study shows the formation of a hitherto unobserved reaction product that could have played a significant role during the emergence of life on the early Earth. We do show that peptide synthesis occurs but with a decrease in the yield. This is due to another concurrent and competing reaction, wherein an amino acid covalently interacts with a phospholipid to generate new amphiphilic species called N-acyl amino acids (NAAs) via an ester-amide exchange process. These NAAs are thermostable and, hence, persistent even at high temperatures. Furthermore, this protoamphiphile is also able to self-assemble into vesicles at acidic pH. Au contraire, fatty acids, a widely accepted constituent of prebiotic compartments, have been shown to generate vesicles only at neutral to alkaline pH. Thus, NAAs could have had a selective advantage over fatty acids to form thermostable protocell compartments under acidic geothermal pool-like conditions, a niche that has gained prominence as one of the important geological settings where life could have originated. Our study underlines the importance of an unbiased exploration of the complex interactions between prebiotic processes, which could potentially open new avenues to solving the origin of life conundrum.

show abstract

“…It was also reported that under prebiotic conditions, amide bonds between fatty acids and amino acids can be formed, producing phosphate-free amphipathic lipoamino acids and lipopeptides. 723 To that end, mixtures of lauric acid with various amino acids heated at 140 °C were studied in the presence or absence of salts and minerals and yielded the formation of lipoamino acids. 723 The same group reported that magnesium and potassium carbonates as well as iron(II) sulfide were particularly useful in these reactions.…”

Section: Covalent Adducts Between Aminomentioning

confidence: 99%

“…723 To that end, mixtures of lauric acid with various amino acids heated at 140 °C were studied in the presence or absence of salts and minerals and yielded the formation of lipoamino acids. 723 The same group reported that magnesium and potassium carbonates as well as iron(II) sulfide were particularly useful in these reactions. In this manner, N-lauroylglycine, N-lauroylalanine, N-stearoylalanine, and several other lipoamino acids have also been generated.…”

Section: Covalent Adducts Between Aminomentioning

confidence: 99%

Prebiotic Peptides: Molecular Hubs in the Origin of Life

et al. 2020

View full text Add to dashboard Cite

The fundamental roles that peptides and proteins play in today’s biology makes it almost indisputable that peptides were key players in the origin of life. Insofar as it is appropriate to extrapolate back from extant biology to the prebiotic world, one must acknowledge the critical importance that interconnected molecular networks, likely with peptides as key components, would have played in life’s origin. In this review, we summarize chemical processes involving peptides that could have contributed to early chemical evolution, with an emphasis on molecular interactions between peptides and other classes of organic molecules. We first summarize mechanisms by which amino acids and similar building blocks could have been produced and elaborated into proto-peptides. Next, non-covalent interactions of peptides with other peptides as well as with nucleic acids, lipids, carbohydrates, metal ions, and aromatic molecules are discussed in relation to the possible roles of such interactions in chemical evolution of structure and function. Finally, we describe research involving structural alternatives to peptides and covalent adducts between amino acids/peptides and other classes of molecules. We propose that ample future breakthroughs in origin-of-life chemistry will stem from investigations of interconnected chemical systems in which synergistic interactions between different classes of molecules emerge.

show abstract

Abiogenic Syntheses of Lipoamino Acids and Lipopeptides and their Prebiotic Significance

Cited by 9 publications

References 43 publications

Spontaneous emergence of membrane-forming protoamphiphiles from a lipid–amino acid mixture under wet–dry cycles

Spontaneous emergence of membrane-forming protoamphiphiles from a lipid–amino acid mixture under wet–dry cycles

Spontaneous Emergence of Membrane-Forming Protoamphiphiles from a Lipid-Amino Acid Mixture Under Wet-Dry Cycles

Prebiotic Peptides: Molecular Hubs in the Origin of Life

Contact Info

Product

Resources

About