Synthesis of Amino Acids from Aldehydes and Ammonia: Implications for Organic Reactions in Carbonaceous Chondrite Parent Bodies

Koga, Tsunenori; Naraoka, Hiroshi

doi:10.1021/acsearthspacechem.2c00008

Cited by 19 publications

(17 citation statements)

References 45 publications

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“…In addition to glycine, d -alanine, sarcosine, d -aspartic acid, and β-alanine are also formed, which may be the result of the reaction of carbohydrates present in the analogue with ammonia or methylamine (Figure ). ,,− This scenario is strengthened by kinetic profiles that show the involvement of carbohydrates in amino-acid formation from a formaldehyde mixture at high temperatures . A rapid increase in amino acid formation is also observed, followed by a rapid decrease of amino-acid abundance in the same time range as observed in our experiment.…”

Section: Discussionsupporting

confidence: 81%

Molecular Diversity and Amino Acid Evolution in Simulated Carbonaceous Chondrite Parent Bodies

Garcia,

Yan,

Meinert

et al. 2024

ACS Earth Space Chem.

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In interplanetary bodies, organics are found originating from various environments. We replicate the solid-phase conditions in a laboratory to elucidate the step-by-step evolution of organic matter, spanning from dense molecular cloud ices to processes occurring within meteorite parent bodies. The focus of our work is on amino acids, considered as potential chemical tracers of secondary alteration on asteroids. Using gas chromatography and high-resolution mass spectrometry, trace amounts of amino acids are identified in a preaccretional organic analogue formed from a dense molecular ice analogue. This analogue was subsequently exposed to aqueous alteration. This induced an increase in the formation of αand βamino acids over time. Supported by high-resolution mass spectrometry data, the reactions involved sugars and amine compounds, followed by amino acid destruction due to the Maillard reaction, which consumes both sugars and amino acids. Surprisingly, a second phase of amino acid formation, specifically α-amino acids, was observed, indicating the potential occurrence of the Strecker reaction. We demonstrate the intricate chemical network occurring within the presence of molecular diversity, similar to what might occur during parent body alteration. Therefore, investigations on reactivity within meteorite parent bodies have to take into account their molecular diversity, recognizing potential cross-reactions, as demonstrated in this work.

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Section: Discussionsupporting

confidence: 81%

Molecular Diversity and Amino Acid Evolution in Simulated Carbonaceous Chondrite Parent Bodies

Garcia,

Yan,

Meinert

et al. 2024

ACS Earth Space Chem.

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“…In the same methanol extract of the Murchison meteorite, N-containing heterocyclic compounds including alkylated pyridines and imidazoles were predominantly present as positive ions, which could be synthesized from formaldehyde and ammonia . It is also known that formaldehyde is an essential starting material to produce key prebiotic organic compounds including amino acids, which have been reported from various classes of meteorites. − In addition, meteoritic IOM might be synthesized by the polymerization of formaldehyde. , Therefore, formaldehyde should play a central role in chemical evolution in primitive asteroids.…”

Section: Discussionmentioning

confidence: 99%

Soluble Sulfur-Bearing Organic Compounds in Carbonaceous Meteorites: Implications for Chemical Evolution in Primitive Asteroids

Naraoka

Hashiguchi

Okazaki

2022

ACS Earth Space Chem.

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Sulfur comprises various compound forms in natural environments and could have played important roles in chemical evolution in the universe. Various soluble organosulfur compounds and inorganic sulfur oxides were identified in the methanol extracts of three carbonaceous chondrites (Murchison, Tagish Lake, and Allende) using high-performance liquid chromatography coupled with high-resolution mass spectrometry. The most abundant S-bearing organic compound was hydroxymethane sulfonic acid (HMSA, HOCH 2 SO 3 H), which is reported from a meteorite for the first time, at a concentration of 201 nmol/g in the Murchison meteorite. Because HMSA is known to be produced by the reaction of formaldehyde (HCHO) and bisulfite (HSO 3 − ), this result indicates that formaldehyde should be abundant prior to the reaction with HSO 3 − in the meteorite parent bodies. The bisulfite derivatives of glycolaldehyde and glyceraldehyde were further identified in the methanol extract, suggesting that the formose reaction had proceeded during the aqueous alteration. The finding of these sugar−HSO 3 − adducts suggests that the formose reaction might have been controlled by the presence of sulfur species in the body. Furthermore, alkylated sulfonic acids (C n H 2n+1 SO 3 H) were also present as a series of homologous compounds up to C 14 in the Murchison meteorite, even though previous studies found only C 1 −C 4 sulfonic acids. In addition to organosulfur compounds, variable inorganic polysulfur oxides and acids were detected. The abundant S-bearing compounds in the meteorites imply important roles of sulfur in the organic reactions in carbonaceous asteroids.

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“…Therefore, these pathways are unfeasible to explain synthesis in meteorite parent bodies. It also remains an open question if alternatives proposed to the Strecker synthesis involving oxygen [91] are plausible in meteorite parent bodies. Dowler et al [92] and Friedmann & Miller [93] demonstrated prebiotic pathways toward vitamin B3 involving precursors formed by electrical discharges.…”

Section: Reaction Pathwaymentioning

confidence: 99%

Possible Ribose Synthesis in Carbonaceous Planetesimals

Paschek

Köhler

Pearce

et al. 2022

Life

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The origin of life might be sparked by the polymerization of the first RNA molecules in Darwinian ponds during wet-dry cycles. The key life-building block ribose was found in carbonaceous chondrites. Its exogenous delivery onto the Hadean Earth could be a crucial step toward the emergence of the RNA world. Here, we investigate the formation of ribose through a simplified version of the formose reaction inside carbonaceous chondrite parent bodies. Following up on our previous studies regarding nucleobases with the same coupled physico-chemical model, we calculate the abundance of ribose within planetesimals of different sizes and heating histories. We perform laboratory experiments using catalysts present in carbonaceous chondrites to infer the yield of ribose among all pentoses (5Cs) forming during the formose reaction. These laboratory yields are used to tune our theoretical model that can only predict the total abundance of 5Cs. We found that the calculated abundances of ribose were similar to the ones measured in carbonaceous chondrites. We discuss the possibilities of chemical decomposition and preservation of ribose and derived constraints on time and location in planetesimals. In conclusion, the aqueous formose reaction might produce most of the ribose in carbonaceous chondrites. Together with our previous studies on nucleobases, we found that life-building blocks of the RNA world could be synthesized inside parent bodies and later delivered onto the early Earth.

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Synthesis of Amino Acids from Aldehydes and Ammonia: Implications for Organic Reactions in Carbonaceous Chondrite Parent Bodies

Cited by 19 publications

References 45 publications

Molecular Diversity and Amino Acid Evolution in Simulated Carbonaceous Chondrite Parent Bodies

Molecular Diversity and Amino Acid Evolution in Simulated Carbonaceous Chondrite Parent Bodies

Soluble Sulfur-Bearing Organic Compounds in Carbonaceous Meteorites: Implications for Chemical Evolution in Primitive Asteroids

Possible Ribose Synthesis in Carbonaceous Planetesimals

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