Proline Behavior in Model Prebiotic Peptides Formed by Wet–Dry Cycling

Ervin, Jabbarrius N.; Bouza, Marcos; Fernández, Facundo M.; Forsythe, Jay G.

doi:10.1021/acsearthspacechem.0c00119

Cited by 6 publications

(4 citation statements)

References 83 publications

(120 reference statements)

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“…Many exciting studies have been reported by simulating prebiotic wet‐dry cycles. [ 64‐67 ] A representation of wet‐dry driven prebiotic peptide formation is shown in Figure 6. Briefly, water evaporation promotes the formation of peptide in the dry phase.…”

Section: Prebiotic Peptide Formationmentioning

confidence: 99%

Prebiotic Chemistry in Aqueous Environment: A Review of Peptide Synthesis and Its Relationship with Genetic Code

et al. 2021

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Amino acids | Peptides | Molecular evolution | Prebiotic chemistry | Genetic code originPrebiotic peptide synthesis and the origin of the genetic code are central issues concerning the origin of life. The question of how they are possibly correlated on the primordial Earth remains perplexing, although numerous experiments have been carried out to explain the prebiotic chemistry of peptide synthesis and the genetic code origin. The purpose of this article is to review the chemical reactions occurred during the synthesis of peptides and the origin of the genetic code in the early Earth aqueous environment. Meanwhile, we attempt to review their relationship as well. At last, from our perspective, the chiral properties of biomolecules should be taken into account in the prebiotic chemical scenarios, which may contribute to some breakthroughs in the further research of this field.

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Section: Prebiotic Peptide Formationmentioning

confidence: 99%

Prebiotic Chemistry in Aqueous Environment: A Review of Peptide Synthesis and Its Relationship with Genetic Code

et al. 2021

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“…Model prebiotic molecules were generated from monomers by wet–dry cycling experiments and DKMs such as 61 identified in the obtained mixtures, in addition to depsipeptides, polyesters, peptides, and yet unreacted hydroxy and amino acids ( Scheme 13 ). 25 …”

Section: Chemical Reactivity and Utilization In Ring-opening Polymerizationsmentioning

confidence: 99%

“…The greater propensity of proline and N -methyl-substituted amino acids to adopt a cis conformation and the consequent preferred DKM cyclization might account for the more frequent appearance of bicyclic DKMs such as 61 ( Scheme 13 ) 25 and N -methyl-substituted DKMs such as 42 – 48 ( Figure 2 ).…”

Section: Natural Productsmentioning

confidence: 99%

Diketomorpholines: Synthetic Accessibility and Utilization

Gütschow

2021

ACS Omega

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Diketomorpholines (DKMs; morpholine-2,5-diones) possess a six-membered ring with a lactone and lactam moiety and belong to the family of cyclodepsipeptides. In this review, the synthetic accessibility of DKMs is summarized and their utilization, in particular, for ring-opening polymerization reactions, is highlighted. The occurrence of the DKM scaffold in natural products encompasses small monocyclic compounds but also complex, polycyclic representatives with a fused DKM ring.

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“…The ubiquity of both water and condensation reactions in the prebiotic formation of biopolymers (as well as the necessity of water for life processes), the so-called water paradox ( 21 ), suggests highly specific conditions and/or the presence of robust and generalizable processes capable of facilitating such chemistry prior to the appearance of proto-enzyme catalysts. This point has been addressed through a variety of approaches which seek to explain the global or localized removal of water from a system to favor condensation ( 16 – 20 , 22 – 27 ).…”

mentioning

confidence: 99%

Aqueous microdroplets enable abiotic synthesis and chain extension of unique peptide isomers from free amino acids

Holden

Morato

Cooks

2022

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

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Amide bond formation, the essential condensation reaction underlying peptide synthesis, is hindered in aqueous systems by the thermodynamic constraints associated with dehydration. This represents a key difficulty for the widely held view that prebiotic chemical evolution leading to the formation of the first biomolecules occurred in an oceanic environment. Recent evidence for the acceleration of chemical reactions at droplet interfaces led us to explore aqueous amino acid droplet chemistry. We report the formation of dipeptide isomer ions from free glycine or L-alanine at the air–water interface of aqueous microdroplets emanating from a single spray source (with or without applied potential) during their flight toward the inlet of a mass spectrometer. The proposed isomeric dipeptide ion is an oxazolidinone that takes fully covalent and ion-neutral complex forms. This structure is consistent with observed fragmentation patterns and its conversion to authentic dipeptide ions upon gentle collisions and for its formation from authentic dipeptides at ultra-low concentrations. It also rationalizes the results of droplet fusion experiments that show that the dipeptide isomer facilitates additional amide bond formation events, yielding authentic tri- through hexapeptides. We propose that the interface of aqueous microdroplets serves as a drying surface that shifts the equilibrium between free amino acids in favor of dehydration via stabilization of the dipeptide isomers. These findings offer a possible solution to the water paradox of biopolymer synthesis in prebiotic chemistry.

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Proline Behavior in Model Prebiotic Peptides Formed by Wet–Dry Cycling

Cited by 6 publications

References 83 publications

Prebiotic Chemistry in Aqueous Environment: A Review of Peptide Synthesis and Its Relationship with Genetic Code

Prebiotic Chemistry in Aqueous Environment: A Review of Peptide Synthesis and Its Relationship with Genetic Code

Diketomorpholines: Synthetic Accessibility and Utilization

Aqueous microdroplets enable abiotic synthesis and chain extension of unique peptide isomers from free amino acids

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