Hypercondensation of an Amino Acid: Synthesis and Characterization of a Black Glycine Polymer

Fox, S. W.; Dalai, Punam; Lambert, Jean-François; Strasdeit, Henry

doi:10.1002/chem.201500820

Cited by 13 publications

(8 citation statements)

References 74 publications

(129 reference statements)

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“…Bulk amino acids can give rise to polymerization reactions but this is often observed at rather high temperatures at which decomposition reactions such as decarboxylation, deamination, or dehydrogenation may be competitive . For instance, depending on the heating conditions, the thermal activation of glycine may result in polypeptides or in a “black polymer” resulting from a high degree of decarboxylation, which is definitely not a polypeptide. On oxide supports such as silica, on the other hand, peptidic condensation occurs at lower temperatures due to catalysis; typically at 150 °C when starting from aqueous solution deposited AAs, or even about 50 °C when depositing the AAs from the gas phase .…”

Section: Introductionmentioning

confidence: 99%

One Step up the Ladder of Prebiotic Complexity: Formation of Nonrandom Linear Polypeptides from Binary Systems of Amino Acids on Silica

Sakhno

Battistella

Mezzetti

et al. 2018

Chemistry A European J

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Evidence for the formation of linearo ligopeptides with nonrandoms equences from mixtures of amino acids coadsorbed on silica ands ubmitted to as imple thermal activation is presented. The amino acid couples (glutamic acid + leucine)a nd (aspartic acid + valine) were deposited on a fumed silica and submitted to as ingle heating step at moderate temperature. The evolution of the systemsw as characterized by X-ray diffraction, infrared spectroscopy,t hermosgravimetric analysis, HPLC, and electrospray ionizationm ass spectrometry (ESI-MS). Evidence for the formation of amide bonds was found in all systemss tudied. Whilet he products of single aminoa cids activation on silica could be consid-ered as evolutionary dead ends, (glutamic acid + leucine) and, at to somee xtent, (aspartic acid + valine) gave rise to the high yield formation of linear peptides up to the hexamers. Oligopeptides of such length have not been observed beforei ns urface polymerization scenarios (unless the amino acids had been depositedb yc hemical vapor deposition, which is not realistic in ap rebiotic environment). Furthermore,n ot all possible amino acid sequences werep resent in the activation products,w hich is indicative of polymerization selectivity.These resultsare promisingf or origins of life studies because they suggest the emergence of nonrandom biopolymers in as imple prebiotic scenario.

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Section: Introductionmentioning

confidence: 99%

One Step up the Ladder of Prebiotic Complexity: Formation of Nonrandom Linear Polypeptides from Binary Systems of Amino Acids on Silica

Sakhno

Battistella

Mezzetti

et al. 2018

Chemistry A European J

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“…(iv) Solid phase. Virtually all types of prebiotically relevant solids can be used, for example, rocks, minerals, meteoritical materials and insoluble organics such as tholins (Sagan & Khare 1979) and thermomelanoids (Fox et al 2015). (v) Volatile products.…”

Section: Resultsmentioning

confidence: 99%

“…As these materials are largely inert, a broad range of acids, bases, salty solutions, organic solvents, gases or gas mixtures can be employed. Solid phase. Virtually all types of prebiotically relevant solids can be used, for example, rocks, minerals, meteoritical materials and insoluble organics such as tholins (Sagan & Khare 1979) and thermomelanoids (Fox et al 2015). Volatile products.…”

Section: Resultsmentioning

confidence: 99%

An automated apparatus for the simulation of prebiotic wet‒dry cycles under strictly anaerobic conditions

Fox

Pleyer

Strasdeit

2018

International Journal of Astrobiology

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Prebiotic chemical evolution on the early Earth may have been driven in part by fluctuating environments, for example wet‒dry and temperature cycling in volcanic rock pools. Here, we describe the setup, operating principle and test applications of a newly developed ‘wet‒dry apparatus’ (WDA) designed to simulate such fluctuating environments. The WDA allows adjusting the duration of the cycles, the temperature during the wet and dry phases and the organic and mineral components, which are all key parameters in wet–dry simulations. The WDA's most important features, however, are (i) that it is automated, which means that long-time experiments are possible without the need for an operator and (ii) that the virtual absence of free oxygen in the early Earth's atmosphere at ground level can be simulated. Rigorously oxygen-free conditions were achieved by passing 99.999% nitrogen gas through two alkaline pyrogallol solutions in series, prior to entering the WDA. We used three chemical systems to test the WDA: (i) the amino acid glycine in the presence and absence of clay minerals, (ii) linoleic acid (an oxygen-sensitive amphiphile) with and without the mineral olivine, and (iii) alkaline pyrogallol solution. We observed that clay minerals greatly accelerated the decomposition of glycine under wet‒dry conditions. Glycine peptides were formed as minor products. In the course of the glycine experiments, we developed a reliable gas chromatographic method to quantify the cyclic dipeptide 2,5-diketopiperazine. The decomposition of linoleic acid in wet‒dry cycles was promoted by both air and olivine. And finally, the extremely oxygen-sensitive pyrogallol solution was used as a colour indicator for residual oxygen in the WDA. The simulation facility in our laboratory currently consists of eight identical WDAs and a surrounding infrastructure. It can be made available to others who wish to perform cyclic wet–dry experiments.

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“…The glycine thermomelanoid may be a good example. Its composition is not well-defined and depends on the formation temperature, the material has a low solubility, and its spectra are not particularly informative ( Fox et al, 2015 ).…”

Section: False Negativesmentioning

confidence: 99%

Inhabited or Uninhabited? Pitfalls in the Interpretation of Possible Chemical Signatures of Extraterrestrial Life

Fox

Strasdeit

2017

Front. Microbiol.

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The “Rare Earth” hypothesis—put forward by Ward and Brownlee in their 2000 book of the same title—states that prokaryote-type organisms may be common in the universe but animals and higher plants are exceedingly rare. If this idea is correct, the search for extraterrestrial life is essentially the search for microorganisms. Various indicators may be used to detect extant or extinct microbial life beyond Earth. Among them are chemical biosignatures, such as biomolecules and stable isotope ratios. The present minireview focuses on the major problems associated with the identification of chemical biosignatures. Two main types of misinterpretation are distinguished, namely false positive and false negative results. The former can be caused by terrestrial biogenic contaminants or by abiotic products. Terrestrial contamination is a common problem in space missions that search for biosignatures on other planets and moons. Abiotic organics can lead to false positive results if erroneously interpreted as biomolecules, but also to false negatives, for example when an abiotic source obscures a less productive biological one. In principle, all types of putative chemical biosignatures are prone to misinterpretation. Some, however, are more reliable (“stronger”) than others. These include: (i) homochiral polymers of defined length and sequence, comparable to proteins and polynucleotides; (ii) enantiopure compounds; (iii) the existence of only a subset of molecules when abiotic syntheses would produce a continuous range of molecules; the proteinogenic amino acids constitute such a subset. These considerations are particularly important for life detection missions to solar system bodies such as Mars, Europa, and Enceladus.

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Hypercondensation of an Amino Acid: Synthesis and Characterization of a Black Glycine Polymer

Cited by 13 publications

References 74 publications

One Step up the Ladder of Prebiotic Complexity: Formation of Nonrandom Linear Polypeptides from Binary Systems of Amino Acids on Silica

One Step up the Ladder of Prebiotic Complexity: Formation of Nonrandom Linear Polypeptides from Binary Systems of Amino Acids on Silica

An automated apparatus for the simulation of prebiotic wet‒dry cycles under strictly anaerobic conditions

Inhabited or Uninhabited? Pitfalls in the Interpretation of Possible Chemical Signatures of Extraterrestrial Life

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