Prebiotic Synthesis of Simple Sugars by an Interstellar Formose Reaction

Jalbout, Abraham F.

doi:10.1007/s11084-008-9151-4

Cited by 13 publications

(9 citation statements)

References 29 publications

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“…The kinetic scheme further suggests that three reaction pathways can contribute to the formation of saturated ketones with the inherent rate constants k 4 to k 6 . The first pathway involves a sequential reaction via an aldehyde and the inherent formation of an RCO radical intermediate (reaction (7)), which then recombines with an alkyl radical (reaction (8)) forming the ketone (k 6 ) (reaction ( 9)).…”

Section: Resultsmentioning

confidence: 99%

“…During the last decade, astronomical observations of simple carbonyl-bearing molecules in the interstellar medium (ISM) such as acetaldehyde (CH 3 CHO), glycolaldehyde (HCOCH 2 OH), methyl formate (HCOOCH 3 ), and acetic acid (CH 3 COOH) have received considerable interest from the astrochemistry and astrobiology communities [1][2][3][4][5][6] because these molecules are considered as key precursors of biologically important molecules such as carbohydrates, 7 amino acids, and polypeptides. 3,8 As the simplest representative of a closed-shell aldehyde, acetaldehyde has emerged as a benchmark molecule since its detection in Sagittarius B2 to understand the astrochemical evolution of cold molecular clouds and of star forming regions.…”

Section: Introductionmentioning

confidence: 99%

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Infrared and reflectron time-of-flight mass spectroscopic analysis of methane (CH₄)–carbon monoxide (CO) ices exposed to ionization radiation – toward the formation of carbonyl-bearing molecules in extraterrestrial ices

Kaiser

Maity

Jones

2014

Phys. Chem. Chem. Phys.

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Ice mixtures of methane and carbon monoxide were exposed to ionizing radiation in the form of energetic electrons at 5.5 K to investigate the formation of carbonyl bearing molecules in extraterrestrial ices. The radiation induced chemical processing of the mixed ices along with their isotopically labeled counterparts was probed online and in situ via infrared spectroscopy (solid state) aided with reflectron time-of-flight mass spectrometry (ReTOFMS) coupled to single photon photoionization (PI) at 10.49 eV (gas phase). Deconvolution of the carbonyl absorption feature centered at 1727 cm(-1) in the processed ices and subsequent kinetic fitting to the temporal growth of the newly formed species suggests the formation of acetaldehyde (CH3CHO) together with four key classes of carbonyl-bearing molecules: (i) alkyl aldehydes, (ii) alkyl ketones, (iii) α,β-unsaturated ketones/aldehydes and (iv) α,β,γ,δ-unsaturated ketones/α,β-dicarbonyl compounds in keto-enol form. The mechanistical studies indicate that acetaldehyde acts as the key building block of higher aldehydes (i) and ketones (ii) with unsaturated ketones/aldehydes (iii) and/or α,β-dicarbonyl compounds (iv) formed from the latter. Upon sublimation of the newly synthesized molecules, ReTOFMS together with isotopic shifts of the mass-to-charge ratios was exploited to identify eleven product classes containing molecules with up to six carbon atoms, which can be formally derived from C1-C5 hydrocarbons incorporating up to three carbon monoxide building blocks. The classes are (i) saturated aldehydes/ketones, (ii) unsaturated aldehydes/ketones, (iii) doubly unsaturated aldehydes/ketones, (iv) saturated dicarbonyls (aldehydes/ketones), (v) unsaturated dicarbonyls (aldehydes/ketones), (vi) saturated tricarbonyls (aldehydes/ketones), molecules containing (vii) one carbonyl - one alcohol (viii), two carbonyls - one alcohol, (ix) one carbonyl - two alcohol groups along with (x) alcohols and (xi) diols. Reaction pathways to synthesize these classes were derived as well. The present experiments provide clear evidence for the formation of key organic molecules--acetaldehyde, acetone, and potentially vinylalcohol--which are among the 15 carbonyl containing organic molecules detected in the interstellar medium. Despite numerous previous experimental investigations probing the effect of ionizing radiation on simple astrophysical ice representatives, our results suggest that more complex organic molecules can be formed in extraterrestrial ices than previously suggested. An outlook on further identification of individual isomers is also presented.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Infrared and reflectron time-of-flight mass spectroscopic analysis of methane (CH₄)–carbon monoxide (CO) ices exposed to ionization radiation – toward the formation of carbonyl-bearing molecules in extraterrestrial ices

Kaiser

Maity

Jones

2014

Phys. Chem. Chem. Phys.

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“…A similar mechanism involving cyanoacetylene (HC 3 N) reacting with either the cyanide anion (OCN − ) or water in the presence of urea (NH 2 CONH 2 ) may also lead to the formation of the nucleobases cytosine and uracil (Ferris et al 1968), which are of great interest to this chapter. Finally, sugars, in particular glucose, ribose, and deoxiribose, as well as their derivatives, could be formed via the formose reaction, i.e., a polymerization of formaldehyde (H 2 CO) (Butlerow 1961;Müller et al 1990;Weber 1998;Jalbout et al 2007Jalbout et al , 2008.…”

Section: Abiotic Chemistry and The Origin Of Life-mentioning

confidence: 99%

Photosynthesis and Photo-Stability of Nucleic Acids in Prebiotic Extraterrestrial Environments

Sandford

Bera

Lee

et al. 2014

Topics in Current Chemistry

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Laboratory experiments have shown that the UV photo-irradiation of low-temperature ices of astrophysical interest leads to the formation of organic molecules, including molecules important for biology such as amino acids, quinones, and amphiphiles. When pyrimidine is introduced in these ices, the products of irradiation include the nucleobases uracil, cytosine, and thymine, the informational sub-units of DNA and RNA, as well as some of their isomers. The formation of these compounds, which has been studied both experimentally and theoretically, requires a succession of additions of OH, NH 2 , and CH 3 groups to pyrimidine. Results show that H 2 O ice plays key roles in the formation of the nucleobases, as an oxidant, as a matrix in which reactions can take place, and as a catalyst that assists proton abstraction from intermiediate compounds. As H 2 O is also the most abundant icy component in most cold astrophysical environments, it probably plays the same roles in space for the formation of biologically relevant compounds. Results also show that although the formation of uracil and cytosine from pyrimidine in ices is fairly straightforward, the formation of thymine is not. This is mostly due to the fact that methylation is a limiting step for its formation, particularly in H 2 O-rich ices, where methylation must competes with oxidation. The relative inefficiency of the abiotic formation of thymine to that of uracil and cytosine, coupled with the fact that thymine has not been detected in meteorites are not inconsistent with the RNA world hypothesis. Indeed, a lack of abiotically produced thymine delivered to the early Earth may have forced the choice for an RNA world, in which only uracil and cytosine are needed, but not thymine.

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“…Formation of prebiotic molecules in extraterrestrial environments has been studied both experimentally and theoretically, demonstrating the synthesis of organic molecules, including molecules important for biology such as amino acids, quinones, and nucleobases. [1][2][3] Methanol ice crystals, as well as other prebiotic building blocks, are ubiquitous in a myriad of interstellar fragments such as comets. [4][5][6] Such entities do not have a protective layer and are thus routinely irradiated with mid/ deep-UV radiation.…”

Section: Introductionmentioning

confidence: 99%

Electron-induced origins of prebiotic building blocks of sugars: mechanism of self-reactions of a methanol anion dimer

Karsili

Fennimore

Matsika

2018

Phys. Chem. Chem. Phys.

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The elementary synthesis of prebiotic molecules has attracted vast attention in recent years. Due to their rich surface chemistry and lack of suitable atmosphere, comets represent an important host for such synthesis, especially since they are routinely irradiated with short wavelength electromagnetic radiation and energetic cosmological electrons. Using high-level electronic structure theory, we present the details of the reactivity associated with the electron-impact induced prebiotic synthesis of ethylene glycol (a carbohydrate building block) from elementary methanol. The results suggest that the experimentally observed intermediates and fragment products can be viably formed by both neutral excited-state chemistry and by dissociative electron attachment - highlighting the importance of a theoretical mapping of the relevant potential energy surfaces that ultimately act as an important guide to the experimental results.

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Prebiotic Synthesis of Simple Sugars by an Interstellar Formose Reaction

Cited by 13 publications

References 29 publications

Infrared and reflectron time-of-flight mass spectroscopic analysis of methane (CH₄)–carbon monoxide (CO) ices exposed to ionization radiation – toward the formation of carbonyl-bearing molecules in extraterrestrial ices

Infrared and reflectron time-of-flight mass spectroscopic analysis of methane (CH₄)–carbon monoxide (CO) ices exposed to ionization radiation – toward the formation of carbonyl-bearing molecules in extraterrestrial ices

Photosynthesis and Photo-Stability of Nucleic Acids in Prebiotic Extraterrestrial Environments

Electron-induced origins of prebiotic building blocks of sugars: mechanism of self-reactions of a methanol anion dimer

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Prebiotic Synthesis of Simple Sugars by an Interstellar Formose Reaction

Cited by 13 publications

References 29 publications

Infrared and reflectron time-of-flight mass spectroscopic analysis of methane (CH4)–carbon monoxide (CO) ices exposed to ionization radiation – toward the formation of carbonyl-bearing molecules in extraterrestrial ices

Infrared and reflectron time-of-flight mass spectroscopic analysis of methane (CH4)–carbon monoxide (CO) ices exposed to ionization radiation – toward the formation of carbonyl-bearing molecules in extraterrestrial ices

Photosynthesis and Photo-Stability of Nucleic Acids in Prebiotic Extraterrestrial Environments

Electron-induced origins of prebiotic building blocks of sugars: mechanism of self-reactions of a methanol anion dimer

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Infrared and reflectron time-of-flight mass spectroscopic analysis of methane (CH₄)–carbon monoxide (CO) ices exposed to ionization radiation – toward the formation of carbonyl-bearing molecules in extraterrestrial ices

Infrared and reflectron time-of-flight mass spectroscopic analysis of methane (CH₄)–carbon monoxide (CO) ices exposed to ionization radiation – toward the formation of carbonyl-bearing molecules in extraterrestrial ices