Simple Organics and Biomonomers Identified in HCN Polymers: An Overview

Ruíz-Bermejo, Marta; Zorzano, María Paz; Osuna‐Esteban, Susana

doi:10.3390/life3030421

Cited by 62 publications

(85 citation statements)

References 99 publications

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“…Figure shows all the compounds identified in this work. Isoserine ( a6 ), iminodiacetic acid ( a8 ), 2,2‐dihydroxyacetic acid ( c2 ), 2,2‐dihydroxymalonic acid ( c4 ), lactic acid ( c5 ), 3‐hydroxypropanoic acid ( c6 ), tartaric acid ( c8 ), glyoxylic acid ( c9 ), pyruvic acid ( c10 ), ketoisovaleric acid ( c11 ), levulinic acid ( c12 ), 2‐ethylmalonic acid ( c17 ), parabanic acid ( h1 ), 5‐hydroxyhydantoin ( h2 ), alloxanic acid ( h3 ), cyanuric acid ( h4 ) and 8‐hydroxyadenine ( h14 ) were identified for the first time in HCN polymers (for a comprehensive list of the monomers previously identified in HCN, please see the Review by Ruiz‐Bermejo et al . Glyoxylic acid ( c9 ) and pyruvic acid ( c10 ) are notably identified as their oxime‐TMS derivatives.…”

Section: Resultsmentioning

confidence: 99%

“…The variation of the reaction time was also studied because most of the reactions to obtain HCN polymers were carried out by using high temperatures and short reaction times (100–80 °C from a few hours to 5–7 days) or at room temperature with longer reaction times (from several weeks to one year), or even at temperatures below 0 °C with reaction times of several years . It is well known that there is a relationship between the reaction time, the temperature and the process of the cyanide polymerization.…”

Section: Resultsmentioning

confidence: 99%

“…All the HCN polymers synthetized herein (using synthetic conditions shown in Table ) were qualitatively analyzed for polar monomers (mainly amino acids, carboxylic acids and N‐heterocycles) by GC‐MS, after acid hydrolysis. It is well‐known that the hydrolysis conditions have a notable influence on the detection, identification and quantification of the monomers present in the HCN polymers …”

Section: Introductionmentioning

confidence: 99%

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The Role of Aqueous Aerosols in the “Glyoxylate Scenario”: An Experimental Approach

Marín-Yaseli

González-Toril

Mompeán

et al. 2016

Chemistry A European J

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The origin of life is one of the fundamental questions in science. Eschenmoser proposed the "glyoxylate scenario", in which plausible abiotic synthesis pathways were suggested to be compatible with the constraints of prebiotic chemistry. In this proposal, the stem compound is HCN. In this work, we explore the "glyoxylate scenario" through several syntheses of HCN polymers, paying particular attention to the role of the aqueous aerosols, together with statistical methods, as a step to elucidate the synthetic problem of the origin of life. The soluble and insoluble HCN polymers synthetized were analyzed by GC-MS. We identified, for the first time, glyoxylic acid in these polymers, together with some constituents of the reductive tricarboxylic acid cycle, amino acids and several N-heterocycles. The findings presented herein, as the first global approach to the "glyoxylate scenario", give full effect to this hypothesis and prove that aqueous aerosols could play an important role in this plausible scene of the origin of life.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Role of Aqueous Aerosols in the “Glyoxylate Scenario”: An Experimental Approach

Marín-Yaseli

González-Toril

Mompeán

et al. 2016

Chemistry A European J

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“…Hydrolysis experiments of the polymers result in the observation of amino acids with particularly significant amounts of glycine and polycyclic nitrogenous compounds such as purines and imidazole derivatives (Supplementary Figure S1). 9,11,[24][25][26][27][28][29][30] Because of these properties, we investigated the AMN polymer as a candidate for a new generic coating method that may be particularly useful in biomedical applications such as cell culture tools, providing high cell attachment and surface coatings on implantable medical devices providing enhanced tissue integration.…”

Section: Introductionmentioning

confidence: 99%

Prebiotic-chemistry inspired polymer coatings for biomedical and material science applications

et al. 2015

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In the field of prebiotic chemistry, hydrogen cyanide (HCN)-derived polymers have been studied for many years as a possible source of the precursors that provide the building blocks for proteins as well as nucleic acids, and they have also been associated with the origin of life. The HCN trimer, aminomalononitrile (AMN), polymerizes to give a brown complex nitrogenous polymer. We report the one-step polymerization-deposition of AMN as a simple generic surface-coating method and as an application of prebiotic chemical research to material science. We found that this polymerization, carried out in buffered aqueous solutions, can be used to coat a wide range of organic and inorganic substrate materials. The robust, non-cytotoxic coatings also provide for excellent cell attachment, suggesting potential biomedical applications. Furthermore, the coating chemistry allows for the immobilization of other compounds, including metals, both during coating formation or by performing secondary immobilization reactions.

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“…HCN is present in comets (6) and is believed to be a key precursor to the origin of life (7)(8)(9)(10)(11). Previous studies have focused on its capability for abiotic synthesis of oxygen-containing molecules (e.g., amino acids and polypeptides), but not on the types of prebiotic chemistry that might occur in oxygen-poor environments.…”

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Polymorphism and electronic structure of polyimine and its potential significance for prebiotic chemistry on Titan

Rahm

Lunine

Usher

et al. 2016

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

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The chemistry of hydrogen cyanide (HCN) is believed to be central to the origin of life question. Contradictions between Cassini-Huygens mission measurements of the atmosphere and the surface of Saturn's moon Titan suggest that HCN-based polymers may have formed on the surface from products of atmospheric chemistry. This makes Titan a valuable "natural laboratory" for exploring potential nonterrestrial forms of prebiotic chemistry. We have used theoretical calculations to investigate the chain conformations of polyimine (pI), a polymer identified as one major component of polymerized HCN in laboratory experiments. Thanks to its flexible backbone, the polymer can exist in several different polymorphs, which are relatively close in energy. The electronic and structural variability among them is extraordinary. The band gap changes over a 3-eV range when moving from a planar sheet-like structure to increasingly coiled conformations. The primary photon absorption is predicted to occur in a window of relative transparency in Titan's atmosphere, indicating that pI could be photochemically active and drive chemistry on the surface. The thermodynamics for adding and removing HCN from pI under Titan conditions suggests that such dynamics is plausible, provided that catalysis or photochemistry is available to sufficiently lower reaction barriers. We speculate that the directionality of pI's intermolecular and intramolecular =N-H … N hydrogen bonds may drive the formation of partially ordered structures, some of which may synergize with photon absorption and act catalytically. Future detailed studies on proposed mechanisms and the solubility and density of the polymers will aid in the design of future missions to Titan.hydrogen cyanide | prebiotic chemistry | Titan | polymers S aturn's moon Titan is a carbon-rich, oxygen-poor world with a wide range of organic compounds, atmospheric energy sources, and alkane liquid seas-all measured by the remarkably successful Cassini-Huygens mission (1). The extreme cold puts liquid water out of reach-buried 50-100 km below a frigid ice crust (2). The lack of liquid water and presence of liquid hydrocarbons makes Titan a unique "natural laboratory" for exploring potential nonterrestrial forms of prebiotic chemistry or, more speculatively, biochemistry, whose essential biopolymers would differ profoundly from terrestrial ones (3). Regardless of the specific chemistry involved, life requires polymorphic molecules that combine flexibility with the ability to form the organized metastable structures needed for function, adaptation, and evolution. This, almost certainly, requires extended molecules capable of intermolecular and intramolecular hydrogen bonding, but such bonds need not involve oxygen; nitrogen is a potential surrogate. Although =N-H . . . N bonds are weaker than those involving oxygen, their energies are large compared with thermal energy (kT ∼ 0.18 kcal/mol at Titan's low temperature, 90-94 K) and intermolecular and intramolecular bonds need not compete with the strong -O-H . ...

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Simple Organics and Biomonomers Identified in HCN Polymers: An Overview

Cited by 62 publications

References 99 publications

The Role of Aqueous Aerosols in the “Glyoxylate Scenario”: An Experimental Approach

The Role of Aqueous Aerosols in the “Glyoxylate Scenario”: An Experimental Approach

Prebiotic-chemistry inspired polymer coatings for biomedical and material science applications

Polymorphism and electronic structure of polyimine and its potential significance for prebiotic chemistry on Titan

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