The Formation and Self‐Assembly of Long Prebiotic Oligomers Produced by the Condensation of Unactivated Amino Acids on Oxide Surfaces

Martra, Gianmario; Deiana, Chiara; Sakhno, Yuriy; Barberis, Ilvis; Fabbiani, Marco; Pazzi, Marco; Vincenti, Marco

doi:10.1002/anie.201311089

Cited by 67 publications

(103 citation statements)

References 26 publications

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“…Recently, Martra et al adsorbed glycine on TiO 2 from the gas phase and subsequently exposed it to water vapour. They observed glycine polymerization (poly-Gly) in a -sheet form [288]. Water vapour adsorption confirmed the expected hydrophobic character of the poly-gly layer.…”

Section: Glycine On Tiomentioning

confidence: 79%

“…The reason is the insulating character of oxides, that makes surface science tools difficult to be used. One exception is TiO 2 , which has a two-fold interest: i) TiO 2 has semi-conducting properties that allow surface science experiments to be performed; ii) it is a highly relevant system for biomolecule adsorption as Ti used as a biomaterial is covered with oxide.In addition, on TiO 2 the gap between gas phase and UHV to liquid phase has been bridged; indeed TiO 2 is of interest for the modelling of prebiotic systems (in gas phase and high temperature conditions) [288]as well as for biomedical applications (in biological solution), thus from the relative simplicity to the extreme complexity.A bottom up approach exists for TiO 2 ,including many surface science studies and different atomistic modelling methods, and studies on TiO 2 are illustrative of the wide range of atomistic modelling tools.…”

Section: Adsorption Of Other Amino Acids At Ni Surfacesmentioning

confidence: 99%

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Adsorption and self-assembly of bio-organic molecules at model surfaces: A route towards increased complexity

Costa

Pradier

Tielens

et al. 2015

Surface Science Reports

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Understanding the bio-physical-chemical interactions at nanostructured biointerfaces and the assembling mechanisms of so-called hybrid nano-composites is nowadays a keyissue for nanoscience in view of the many possible applications foreseen. The contribution of surface science in this field is noteworthy since, using a bottom-up approach, it allows the investigation of the fundamental processes at the basis of complex interfacial phenomena and thus it helps to unravelthe elementary mechanisms governing them. Nowadays it is well demonstrated that a wide variety of different molecular assemblies can form upon adsorption of small biomolecules at surfaces. The geometry of such self-organized structures can often be tuned by a careful control of the experimental conditions during the deposition process. Indeed an impressive number of studies exist (both experimental and -to a lesser extendtheoretical), which demonstrate the ability of molecular self-assembly to create different structural motifs in a more or less predictable manner, by tuning the molecular building blocks as well as the metallic substrate. In this frame, amino acidsand small peptides at surfaces are key, basic, systems to be studied. The amino acidsstructure is simple enough to serve as a model for the chemisorption of biofunctional molecules, but their adsorption at surfaces has applications in surface functionalization, in enantiospecific catalysis, biosensing, nanoparticles shape control or in emerging fields such as "green" corrosion inhibition. In this paper we review the most recent advancements in this field. We will start from amino acids adsorption at metal surfaces and we will evolve then in the direction of more complex systems, in thelight of the latest improvements of surface science techniques and of computational methods. On one side, we will focus on amino acids adsorption at oxide surfaces, on the other on peptide adsorption both at metal and oxide substrates. Particular attention will be drawn to the added value provided by the combination of several experimental surface science techniques and to the precious contribution of advanced complementary computational methods to resolve the details of systems of increased complexity. Finally, some hints into experiments performed in the presence of water and then characterized in UHV and in the related theoretical work will be presented. This is a further step towards abetter approximation of real biological systems. However, since the methods employed are often not typical of surface science, this topic is not developed in details.2

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Section: Glycine On Tiomentioning

confidence: 79%

Section: Adsorption Of Other Amino Acids At Ni Surfacesmentioning

confidence: 99%

Adsorption and self-assembly of bio-organic molecules at model surfaces: A route towards increased complexity

Costa

Pradier

Tielens

et al. 2015

Surface Science Reports

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“…Consequently, researchers have long sought a plausible prebiotic reaction that would have condensed free AAs into peptides . However, the polycondensation of nonactivated AAs is thermodynamically unfavored in aqueous solution, and only proceeds in the dry state at elevated temperatures (e.g., 130 °C) or by vapor deposition on catalytic surfaces . In addition to the challenge of peptide bond formation, AA dimers have a strong propensity to cyclize, forming diketopiperazines, which greatly hinders the formation of longer peptides.…”

Section: Figurementioning

confidence: 99%

“…Studies of amide bond formation involving carboxylic acids and amines on metal oxides, such as TiO 2 , have shown evidence of surface carboxylates as activated electrophilic species . Thus, mineral‐catalyzed reactions and the above‐mentioned HA‐catalyzed reaction might act through a common mechanism of ester–amide exchange.…”

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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“…Finally, very recent results regarding polyglycine formed on titania indicated that the oligomers interacting with the titania surface seem to have a well-defined secondary structure containing both -helices and -sheets, judging from the shape of their IR bands [37]. This is important since this kind of structural elements play a fundamental role in defining the reactivity of proteins: thus, the functional elements of protein may have already been in place at this step.…”

Section: Polymerization Selectivity and Organizationmentioning

confidence: 99%

Origins of life: From the mineral to the biochemical world

Lambert

2015

BIO Web of Conferences

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Abstract.In this brief review, we summarize the most influential scenarios in origins-oflife studies that have resorted to minerals surfaces. The influence of the pre-existing mineral world on the organization of matter towards the living state may have manifested at several steps in the rise towards higher complexity. Small biomolecules such as amino acids formed on mineral surfaces of interstellar dust, meteorites or comets prior to their delivery to the primordial Earth. Mineral surfaces are known to promote the polymerization of these small molecules to the corresponding biopolymers (e.g. amino acids to proteins), and they may have oriented this polymerization to the formation of specific structures. Crucial steps of protometabolism could have originated on the surface of sulfide minerals. The most daring view of the prebiotic role of minerals holds that some of them may have carried genetic information subject to darwinian selection prior to the rise of nucleic acids, today's genetic material. Finally, porous structures ranging from the nanometer to the micrometer probably helped protect the first proto-organisms from dilution and other damage. Future studies are expected to see progress towards molecular-level characterization, and to start accounting for the complexity of the prebiotic environment.

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The Formation and Self‐Assembly of Long Prebiotic Oligomers Produced by the Condensation of Unactivated Amino Acids on Oxide Surfaces

Cited by 67 publications

References 26 publications

Adsorption and self-assembly of bio-organic molecules at model surfaces: A route towards increased complexity

Adsorption and self-assembly of bio-organic molecules at model surfaces: A route towards increased complexity

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

Origins of life: From the mineral to the biochemical world

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