Quantitation of α‐hydroxy acids in complex prebiotic mixtures via liquid chromatography/tandem mass spectrometry

Parker, Eric T.; Cleaves, H. James; Bada, Jeffrey L.; Fernández, Facundo M.

doi:10.1002/rcm.7684

Cited by 36 publications

(31 citation statements)

References 42 publications

(81 reference statements)

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“…Classical approaches in OoL have often been constrained to biomolecules due to their ubiquity in biology, however, most of these biomolecules were not necessarily available at early prebiotic stages [136]. Prebiotic environments most likely included compounds not central to modern biopolymers, for example, alpha hydroxy acids (aHA) [137] among numerous others [138,139]. Recent work has shown that aHAs easily form combinatorial polyesters under wet-dry conditions that may have played a role in the catalytic landscape within which they were formed [140].…”

Section: On the Right Track? Looking At The Past Decadementioning

confidence: 99%

The Future of Origin of Life Research: Bridging Decades-Old Divisions

Preiner

Asche

Becker

et al. 2020

Life

118

150

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Research on the origin of life is highly heterogeneous. After a peculiar historical development, it still includes strongly opposed views which potentially hinder progress. In the 1st Interdisciplinary Origin of Life Meeting, early-career researchers gathered to explore the commonalities between theories and approaches, critical divergence points, and expectations for the future. We find that even though classical approaches and theories—e.g., bottom-up and top-down, RNA world vs. metabolism-first—have been prevalent in origin of life research, they are ceasing to be mutually exclusive and they can and should feed integrating approaches. Here we focus on pressing questions and recent developments that bridge the classical disciplines and approaches, and highlight expectations for future endeavours in origin of life research.

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Section: On the Right Track? Looking At The Past Decadementioning

confidence: 99%

The Future of Origin of Life Research: Bridging Decades-Old Divisions

Preiner

Asche

Becker

et al. 2020

Life

118

150

View full text Add to dashboard Cite

show abstract

“…microscale compartments from diverse pools of simple chemicals is warranted. In this sense, the ubiquity and diversity of α-hydroxy acids (αHAs) in various primitive environments is well known, as they are synthesized in various abiotic systems such as spark discharge experiments (17) and found in carbonaceous meteorites (18,19). Recently, Chandru et al (20) showed that αHAs readily form combinatorial polymer libraries under evaporative conditions, which could reasonably have been synthesized on early Earth or other watery rocky planets, such as Mars (21) or even those of the TRAPPIST-1 system (22), through diurnal or seasonal oscillations in insolation (23).…”

Section: Significancementioning

confidence: 99%

Membraneless polyester microdroplets as primordial compartments at the origins of life

Jia

Chandru

Hongo

et al. 2019

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

Self Cite

111

146

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Compartmentalization was likely essential for primitive chemical systems during the emergence of life, both for preventing leakage of important components, i.e., genetic materials, and for enhancing chemical reactions. Although life as we know it uses lipid bilayer-based compartments, the diversity of prebiotic chemistry may have enabled primitive living systems to start from other types of boundary systems. Here, we demonstrate membraneless compartmentalization based on prebiotically available organic compounds, α-hydroxy acids (αHAs), which are generally coproduced along with α-amino acids in prebiotic settings. Facile polymerization of αHAs provides a model pathway for the assembly of combinatorially diverse primitive compartments on early Earth. We characterized membraneless microdroplets generated from homo- and heteropolyesters synthesized from drying solutions of αHAs endowed with various side chains. These compartments can preferentially and differentially segregate and compartmentalize fluorescent dyes and fluorescently tagged RNA, providing readily available compartments that could have facilitated chemical evolution by protecting, exchanging, and encapsulating primitive components. Protein function within and RNA function in the presence of certain droplets is also preserved, suggesting the potential relevance of such droplets to various origins of life models. As a lipid amphiphile can also assemble around certain droplets, this further shows the droplets’ potential compatibility with and scaffolding ability for nascent biomolecular systems that could have coexisted in complex chemical systems. These model compartments could have been more accessible in a “messy” prebiotic environment, enabling the localization of a variety of protometabolic and replication processes that could be subjected to further chemical evolution before the advent of the Last Universal Common Ancestor.

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“…This reaction is of potential prebiotic relevance because 1) the reaction proceeds with AAs that are not preactivated, at temperatures as low 65 °C; and 2) HAs are also considered plausible prebiotic molecules because they are found together with AAs in meteorites. Both AAs and HAs are also among the products of spark discharge experiments . Upon drying and heating, ester bonds are formed by the hydroxyl group of HA residues with HA and AA carboxylic acid groups, and facilitate amide bond formation through nucleophilic attack by the amino group of an AA.…”

Section: Figurementioning

confidence: 99%

A Possible Path to Prebiotic Peptides Involving Silica and Hydroxy Acid‐Mediated Amide Bond Formation

McKee

Solano

Saydjari³

et al. 2018

ChemBioChem

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The formation of alanine and glycine oligomers in films produced by drying aqueous mixtures of lactic acid and silica nanoparticles has been studied as a model prebiotic reaction. The addition of silica results in alanine or glycine enrichment in the polymers. Oligomerization proceeds through ester-mediated peptide bond formation in an acidic and evaporative environment at temperatures as low as 85 °C. For both amino acids, the dominant species produced in the presence of silica and lactic acid are rich in amide bonds and deficient in ester linkages. At higher temperatures, glycine and alanine oligomers contain only a single hydroxy acid residue conjugated to the peptide N terminus. Similar product distributions occur with silica particles prereacted with lactic acid, which suggests the catalytic role of a functionalized surface. This work highlights the role minerals might have served in transitioning from oligomers with both ester and amide linkages (depsipeptides) to peptides in a prebiotic context.

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Quantitation of α‐hydroxy acids in complex prebiotic mixtures via liquid chromatography/tandem mass spectrometry

Cited by 36 publications

References 42 publications

The Future of Origin of Life Research: Bridging Decades-Old Divisions

The Future of Origin of Life Research: Bridging Decades-Old Divisions

Membraneless polyester microdroplets as primordial compartments at the origins of life

A Possible Path to Prebiotic Peptides Involving Silica and Hydroxy Acid‐Mediated Amide Bond Formation

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