Synthesis of β-Peptide Standards for Use in Model Prebiotic Reactions

Forsythe, Jay G.; English, Sloane L.; Simoneaux, Rachel E.; Weber, Arthur L.

doi:10.1007/s11084-018-9558-5

Cited by 4 publications

(8 citation statements)

References 32 publications

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“…The formation of β-peptides under model prebiotic conditions was also demonstrated. − For instance, β-glutamic acid readily oligomerizes in the presence of the water-soluble carbodiimide 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (EDAC) at −20 °C . In a subsequent study, the oligomerization of α-amino acids was compared with that of β-amino acids in aqueous solution using two different condensing agents .…”

Section: Alternative Proto-peptidesmentioning

confidence: 99%

Prebiotic Peptides: Molecular Hubs in the Origin of Life

et al. 2020

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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.

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Section: Alternative Proto-peptidesmentioning

confidence: 99%

Prebiotic Peptides: Molecular Hubs in the Origin of Life

et al. 2020

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“…Each carbon-carbon bond within the amino acid backbone permits rotation that increases the flexibility of a peptide chain [75][76][77] (also see Figure 3). But while the lack of backbone rigidity has long been noted as one simple reason why natural selection would favor α-amino acids for the genetic code [10], synthetic biology demonstrates that β-amino acid peptide structures are possible [78][79][80]. Thus, arguments for the exclusion of β-, γ-, and δ-amino acids from the genetic code again resemble those for homochirality: a more robust explanation than strict biophysical constraint is evolutionary optimization.…”

Section: α-Amino Acids Versus Longer Backbonesmentioning

confidence: 99%

Xeno Amino Acids: A Look into Biochemistry as We Do Not Know It

Brown,

Mayer-Bacon,

Freeland

2023

Life

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Would another origin of life resemble Earth’s biochemical use of amino acids? Here, we review current knowledge at three levels: (1) Could other classes of chemical structure serve as building blocks for biopolymer structure and catalysis? Amino acids now seem both readily available to, and a plausible chemical attractor for, life as we do not know it. Amino acids thus remain important and tractable targets for astrobiological research. (2) If amino acids are used, would we expect the same L-alpha-structural subclass used by life? Despite numerous ideas, it is not clear why life favors L-enantiomers. It seems clearer, however, why life on Earth uses the shortest possible (alpha-) amino acid backbone, and why each carries only one side chain. However, assertions that other backbones are physicochemically impossible have relaxed into arguments that they are disadvantageous. (3) Would we expect a similar set of side chains to those within the genetic code? Many plausible alternatives exist. Furthermore, evidence exists for both evolutionary advantage and physicochemical constraint as explanatory factors for those encoded by life. Overall, as focus shifts from amino acids as a chemical class to specific side chains used by post-LUCA biology, the probable role of physicochemical constraint diminishes relative to that of biological evolution. Exciting opportunities now present themselves for laboratory work and computing to explore how changing the amino acid alphabet alters the universe of protein folds. Near-term milestones include: (a) expanding evidence about amino acids as attractors within chemical evolution; (b) extending characterization of other backbones relative to biological proteins; and (c) merging computing and laboratory explorations of structures and functions unlocked by xeno peptides.

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Section: Introductionmentioning

confidence: 99%

“…Several reports have discussed the formation of peptides containing beta amino acids in model abiotic reactions [54][55][56][57][58][59][60][61][62][63]. For instance, it has been shown that β-alanine is polymerized into β-peptides during wet-dry cycling in the presence of glycerol and sodium biocarbonate [54]. In addition, polymerization was demonstrated with beta amino acids activated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC) [55,56] and by the methyl ester forms of beta amino acids [54].…”

Section: Introductionmentioning

confidence: 99%

“…For instance, it has been shown that β-alanine is polymerized into β-peptides during wet-dry cycling in the presence of glycerol and sodium biocarbonate [54]. In addition, polymerization was demonstrated with beta amino acids activated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC) [55,56] and by the methyl ester forms of beta amino acids [54]. Moreover, alpha amino acids have different inherent polymerization behaviors to analogous beta and gamma amino acids [58,59].…”

Section: Introductionmentioning

confidence: 99%

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Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions

Frenkel-Pinter

Jacobson

Eskew-Martin

et al. 2022

Life

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The origin of biopolymers is a central question in origins of life research. In extant life, proteins are coded linear polymers made of a fixed set of twenty alpha-L-amino acids. It is likely that the prebiotic forerunners of proteins, or protopeptides, were more heterogenous polymers with a greater diversity of building blocks and linkage stereochemistry. To investigate a possible chemical selection for alpha versus beta amino acids in abiotic polymerization reactions, we subjected mixtures of alpha and beta hydroxy and amino acids to single-step dry-down or wet-dry cycling conditions. The resulting model protopeptide mixtures were analyzed by a variety of analytical techniques, including mass spectrometry and NMR spectroscopy. We observed that amino acids typically exhibited a higher extent of polymerization in reactions that also contained alpha hydroxy acids over beta hydroxy acids, whereas the extent of polymerization by beta amino acids was higher compared to their alpha amino acid analogs. Our results suggest that a variety of heterogenous protopeptide backbones existed during the prebiotic epoch, and that selection towards alpha backbones occurred later as a result of polymer evolution.

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Synthesis of β-Peptide Standards for Use in Model Prebiotic Reactions

Cited by 4 publications

References 32 publications

Prebiotic Peptides: Molecular Hubs in the Origin of Life

Prebiotic Peptides: Molecular Hubs in the Origin of Life

Xeno Amino Acids: A Look into Biochemistry as We Do Not Know It

Differential Oligomerization of Alpha versus Beta Amino Acids and Hydroxy Acids in Abiotic Proto-Peptide Synthesis Reactions

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