Ribose and related sugars from ultraviolet irradiation of interstellar ice analogs

Meinert, Cornelia; Myrgorodska, Iuliia; Marcellus, Pierre de; Buhse, Thomas; Nahon, Laurent; Hoffmann, Søren Vrønning; d’Hendecourt, Louis Le Sergeant; Meierhenrich, Uwe J.

doi:10.1126/science.aad8137

Cited by 257 publications

(246 citation statements)

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“…Recent analysis of a suite of soluble compounds from CR meteorites led researchers to conclude that a fraction of the compounds (including sugar alcohols) were formed before any possible onset of aqueous alteration in the parent bodies and could therefore have origins in preaccretion environments: Some of the meteorites showed little or no evidence of the action of liquid water (12). Consistent with these findings, recent laboratory experiments designed to simulate the low-temperature irradiation of organic precursors on interstellar grains produced a suite of larger polyols, including multiple sugars (35,36). In the case of formaldehyde, a precursor to polyols, simulations using IR detection have shown that formaldehyde/NH 3 /H 2 O mixtures start to form compounds down to at least 40 K, i.e., temperatures relevant to interstellar/presolar grains (37).…”

Section: Resultssupporting

confidence: 58%

Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites

Cooper

Rios

2016

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

123

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Biological polymers such as nucleic acids and proteins are constructed of only one-the D or L-of the two possible nonsuperimposable mirror images (enantiomers) of selected organic compounds. However, before the advent of life, it is generally assumed that chemical reactions produced 50:50 (racemic) mixtures of enantiomers, as evidenced by common abiotic laboratory syntheses. Carbonaceous meteorites contain clues to prebiotic chemistry because they preserve a record of some of the Solar System's earliest (∼4.5 Gy) chemical and physical processes. In multiple carbonaceous meteorites, we show that both rare and common sugar monoacids (aldonic acids) contain significant excesses of the D enantiomer, whereas other (comparable) sugar acids and sugar alcohols are racemic. Although the proposed origins of such excesses are still tentative, the findings imply that meteoritic compounds and/or the processes that operated on meteoritic precursors may have played an ancient role in the enantiomer composition of life's carbohydrate-related biopolymers.carbonaceous meteorites | sugar acids | enantiomer excesses | aldonic acids | polyols T he organic phase of carbonaceous meteorites comprises an insoluble "macromolecular" material (1-3), a complex mixture of largely uncharacterized solvent-extractable compounds (4), as well as discrete (identified) soluble organic compounds such as amino acids (3, 5) nucleobases (6, 7), and sugar derivatives (8). Analyses of this prebiotic organic carbon have been important in understanding its early Solar System synthesis and history: Characteristics of the organic phase suggest that it consists of both products and survivors of interstellar/presolar grain irradiation (9) and subsequent encapsulation and aqueous reactions (10, 11) in asteroids "parent bodies."Several identified meteoritic organic compounds are chiral: They can exist as two nonsuperimposable mirror image compounds called enantiomers, commonly designated D and L. To date, most chiral meteoritic compounds are reported to be racemic mixtures, i.e., their D and L enantiomers are equal in abundance (3). Racemic compounds are expected in nature because typical abiotic synthetic processes are (historically) thought to occur in the absence of asymmetric influences. Racemic mixtures are equated with pristine/uncontaminated abiotic samples when discussing meteoritic compounds. However, some meteoritic amino acids that are rare on Earth, i.e., they are not constituents of proteins and therefore less likely to be contaminants, have been confirmed to contain L enantiomer excesses (EE) (3, 12, 13). The origins of such excesses are unknown.Sugars, aldehydes, or ketones that contain multiple carbon hydroxyl (carbon alcohol) groups, are also chiral and were likely necessary for the origin of life. In the majority of extant biological sugars and derivatives ("polyols"), the D enantiomers are significantly more abundant than the L enantiomers (we will note exceptions in Results and Natural Occurrence of Relevant Sugar Derivatives and Enantiomers)...

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Section: Resultssupporting

confidence: 58%

Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites

Cooper

Rios

2016

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

123

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“…[1][2][3][4][5][6][7]13,[15][16][17][18][19][20][21] A separate synthesis of pure glycolaldehyde (2a) and glyceraldehyde (2b) is ostensively implausible, therefore a means of physical separation is better suited to promote the desired selective and sequential delivery of these simple sugars. 6,14,28 Our attention was first drawn to the possible role of 2-aminothiazole (7) in mediating the sequestration, separation and accumulation of glycolaldehyde (2a) and glyceraldehyde (2b) when we observed precipitation of glycolaldehyde (2a) and homochiral D-glyceraldehyde (D-2b) from water as aminals 8a and D-8b.…”

Section: Resultsmentioning

confidence: 99%

Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures

2017

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UK 2A central problem for prebiotic synthesis of the biological amino acids and nucleotides is avoiding the concomitant synthesis of undesired or irrelevant byproducts. Additionally, multistep pathways require mechanisms that enable the sequential addition of reactants and purification of intermediates that are consistent with reasonable geochemical scenarios. Here, we show that 2-aminothiazole reacts selectively with two-and three-carbon sugars (glycolaldehyde and glyceraldehyde, respectively), which results in their accumulation and purification as stable crystalline aminals. This permits ribonucleotide synthesis, even from complex sugar mixtures. Remarkably, aminal formation also overcomes the thermodynamically favoured isomerisation of glyceraldehyde to dihydroxyacetone because only the aminal of glyceraldehyde separates from the equilibrating mixture. Finally, we show that aminal formation provides a novel pathway to amino acids that avoids synthesis of the non-proteinogenic α,α-disubstituted analogues. The common physicochemical mechanism that controls proteinogenic amino acid and ribonucleotide assembly from prebiotic mixtures suggests these essential classes of metabolite had a unified chemical origin. 3The conservation of the genetic code, amino acids, and nucleotides in biology suggests a single origin of life on Earth. [1][2][3][4][5][6][7][8][9][10][11][12][13] Proteins are built from a highly restricted set of about 20 amino acids according to a universal triplet code of four ribonucleotides. Therefore, it is essential to learn how this specific small constellation of molecules became irrevocably linked at the advent of life. In contrast to the narrow distribution of universal metabolites observed in biology, typical prebiotic reactions are notorious for their complex product distributions. Accordingly, it has been recognised that "the chief obstacle to understanding the origin of RNA-based life is identifying a plausible mechanism for overcoming the clutter wrought by prebiotic chemistry". [4][5][6][7] For example, the most-efficient and specific proposed prebiotic pathway to the pyrimidine ribonucleotides requires synthesis of the key intermediate pentose aminooxazoline (1) (Fig. 1a). [2][3][4][5][6][22][23][24] However, the plausibility of this proposed prebiotic synthesis of pentose aminooxazoline (1) has been questioned because it is contingent upon the strictly controlled sequential delivery of pure glycolaldehyde (2a) to cyanamide (3) to yield 2-aminooxazole (4), followed by pure glyceraldehyde (2b) to 2-aminooxazole (4) to yield the desired product (Fig. 1a). This is a serious problem because both of these reactions lack the intrinsic selectivity required to exclusively yield their respective products (2-aminooxazole (4) and pentose aminooxazoline (1)) from mixtures of glycolaldehyde (2a) and glyceraldehyde (2b). The problem becomes increasingly worse in the presence of other sugars. Without a separate and sequential delivery of glycolaldehyde (2a) and glyceraldehyde (2b), a complex mixture...

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“…Schematic of the experimental set-up from Briani et al 2013 of ribonucleotides in a particularly primitive Earth-like environment (Powner et al 2009), were found (de Marcellus et al 2015). More recently, the detection of the aldopentose ribose together with a full family of structurally related sugar molecules have been reported in quite high abundances in the same laboratory ices (Meinert et al 2016). One may also note that nucleobases are suspected to be present in the residue.…”

Section: Interstellar and Cometary Organic Chemistry Simulation Facilmentioning

confidence: 99%

Earth as a Tool for Astrobiology—A European Perspective

et al. 2017

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Scientists use the Earth as a tool for astrobiology by analyzing planetary field analogues (i.e. terrestrial samples and field sites that resemble planetary bodies in our Solar System). In addition, they expose the selected planetary field analogues in simulation chambers to conditions that mimic the ones of planets, moons and Low Earth Orbit (LEO) space conditions, as well as the chemistry occurring in interstellar and cometary ices. This paper reviews the ways the Earth is used by astrobiologists: (i) by conducting planetary field analogue studies to investigate extant life from extreme environments, its metabolisms, adaptation strategies and modern biosignatures; (ii) by conducting planetary field analogue studies to investigate extinct life from the oldest rocks on our planet and its biosignatures; (iii) by exposing terrestrial samples to simulated space or planetary environments and producing a sample analogue to investigate changes in minerals, biosignatures and microorganisms. The European Space Agency (ESA) created a topical team in 2011 to investigate recent activities using the Earth as a tool for astrobiology and to formulate recommendations and scientific needs to improve ground-based astrobiological research. Space is an important tool for astrobiology (see Horneck et al. in Astrobiology, 16:201-243, 2016;Cottin et al., 2017), but access to space is limited. Complementing research on Earth provides fast access, more replications and higher sample throughput. The major conclusions of the topical team and suggestions for the future include more scientifically qualified calls for field campaigns with planetary analogy, and a centralized point of contact at ESA or the EU for the organization of a survey of such expeditions. An improvement of the coordinated logistics, infrastructures and funding system supporting the combination of field work with planetary simulation investigations, as well as an optimization of the scientific return and data processing, data storage and data distribution is also needed. Finally, a coordinated EU or ESA education and outreach program would improve the participation of the public in the astrobiological activities.

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Ribose and related sugars from ultraviolet irradiation of interstellar ice analogs

Cited by 257 publications

References 42 publications

Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites

Enantiomer excesses of rare and common sugar derivatives in carbonaceous meteorites

Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures

Earth as a Tool for Astrobiology—A European Perspective

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