Amino Acid Analyses of the Murchison, Murray, and Allende Carbonaceous Chondrites

Cronin, John R.; Moore, C. B.

doi:10.1126/science.172.3990.1327

Cited by 219 publications

(95 citation statements)

References 10 publications

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“…All of the aliphatic a-amino acids reported in the Murchison Meteorite (25)(26)(27)(28), as well as aspartic acid, glutamic acid, ,+alanine, and proline, were obtained in this electric-discharge experiment. We have also found N-alkylated amino acids, as well as other nonprotein amino acids, in these experiments.…”

Section: Discussionmentioning

confidence: 99%

Prebiotic Synthesis of Hydrophobic and Protein Amino Acids

Ring

Wolman

Friedmann

et al. 1972

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

161

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The formation of amino acids by the action of electric discharges on a mixture of methane, nitrogen, and water with traces of ammonia was studied in detail. The presence of glycine, alanine, a-amino-n-butyric acid, a-aminoisobutyric acid, valine, norvaline, isovaline, leucine, isoleucine, alloisoleucine, norleucine, proline, aspartic acid, glutamic acid, serine, threonine, allothreonine, a-hydroxy---aminobutyric acid, and a,-y-diaminobutyric acid was confirmed by ion-exchange chromatography and gas chromatography-mass spectrometry. All of the primary a-amino acids found in the Murchison Meteorite have been synthesized by this electric discharge experiment.Most prebiotic syntheses that start with the primitive atmospheric constituents give substantial yields of glycine, alanine, and a-amino-n-butyric acid (1). Prebiotic syntheses of the higher aliphatic amino acids have been claimed, for example, by the action of electric discharges on CH4 + NH3 + H20 (2-6), by heating CH4 + NH3 + H20 to 900-1200°(7, 8), and by the action of shock waves on CH4, C2H6, NH3, and H20 (9). The amino acids were identified only by an amino-acid analyzer (2-4, 6, 7, 9), only by paper electrophoresis (8), or only by gas chromatography (5). However, these techniques are not sufficient by themselves to identify an amino acid.In the original synthesis of amino acids by electric discharges (10-12), only glycine, alanine, a-amino-t-butyric acid, a-aminoisobutyric acid, and ,B-alanine, of the simple aliphatic amino acids, were synthesized in sufficient yield to obtain identification by a melting point of a derivative. Recently developed techniques permit the identification of compounds found in lower yield by this synthesis.The synthesis under prebiotic conditions of aspartic and glutamic acid (2-8, 12-14), serine (2, 5, 6-8, 13), threonine (2, 3, 5-7), and proline (3, 4, 7, 8, 13) have been reported but they have not been properly identified [except for aspartic acid (14) ]. The synthesis of these amino acids (except proline) has also been reported from the polymerization of HCN (1), but again without proper identification. A prebiotic synthesis of threonine should also yield allothreonine, but this amino acid has never been reported. In addition, several investigators have reported the appearance of a large peak at the isoleucine position on the amino-acid analyzer (2, 4-6, 13). The identification of this peak as isoleucine has been questioned (4, 13). It is evident that this compound cannot be isoleucine, since a corresponding peak for alloisoleucine is not observed.Most electric-discharge experiments have been done with a large amount of ammonia present. Use of nitrogen instead of ammonia in such experiments does not change the major products, although the yield of amino acids is lower (12).The use of a higher concentration of ammonia in such experiments has been criticized (15), and it is now thought that the ammonia concentration in the prebiotic atmosphere was not likely to have been greater than 10-5 atm (16,17). Although this i...

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Section: Discussionmentioning

confidence: 99%

Prebiotic Synthesis of Hydrophobic and Protein Amino Acids

Ring

Wolman

Friedmann

et al. 1972

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

161

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“…Chirality DOI 10.1002/chir [7] L-Ala (5.280), [8] D-Ala, [9] DL-Thr (OH-free), [10] L-Leu (1.000), [11] values m/z ¼ 279 for Thr, m/z ¼ 282 for Leu, and m/z ¼ 238 for Ser. In conclusion, it was possible to separate 13 enantiomeric pairs, 9 of which had acceptable Rs values (higher than 1.2).…”

Section: Separation On Chirasil-l-valmentioning

confidence: 99%

“…In meteorites found on Earth, amino acids that are common to biological systems are either present in trace amounts (e.g., Ser, Thr) or absent (e.g., Tyr, Phe, Met, Cys, Lys, His, Arg). [7][8][9][10][11][12][13][14][15][16] The principal common amino acids detected were Glu, Asp, Pro, Gly, b-Ala, Ile, Leu, Sar, Ala, Val, and rare or uncommon amino acids: a-aminoisobutyric acid, a-amino-n-butyric acid, isovaline, other N-alkyl amino acids and a-dialkyl amino acids, more resistant to racemization phenomena than the a-alkyl amino acids. Therefore most of them were aliphatic amino acids, which are well detected using the proposed 1-step method.…”

Section: Quantitative Analysismentioning

confidence: 99%

“…With this aim, detection of chemical biomarkers, i.e., of organic molecules that play an important role in biochemistry, will be one of the main goals of future space missions. Among the key chemical biomarkers on Earth, [1][2][3] amino and carboxylic acids which have been synthesized by experimental simulations under plausible prebiotic conditions, [4][5][6] have been detected in several meteorites [7][8][9][10][11][12][13] and in the lunar soil. [14][15][16] Thus, these chemical species appear to be widespread in the solar system, but they can exist without the presence of life.…”

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confidence: 99%

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GC‐MS analysis of amino acid enantiomers as their N(O,S)‐perfluoroacyl perfluoroalkyl esters: Application to space analysis

et al. 2006

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The target of the in-situ research of optical activity in extraterrestrial samples stimulated an extended investigation of a GC-MS method based on the derivatization of amino acids by using a mixture of perfluorinated alcohols and perfluorinated anhydrides. Amino acids are converted to their N(O,S)-perfluoroacyl perfluoroalkyl esters in a single-step procedure, using different combinations of the derivatization reagents trifluoroacetic anhydride (TFAA)-2,2,2-trifluoro-1-ethanol (TFE), 2,3,3,4,4,, and heptafluorobutyric anhydride (HFBA)-HFB. The derivatives obtained are analyzed using two different chiral columns: Chirasil-L-Val and g-cyclodextrin (Rt-g-DEXsa) stationary phases which show different and complementary enantiomeric selectivity. The mass spectra of the derivatives are studied, and mass fragmentation patterns are proposed: significant fragment ions can be identified to detect amino acid derivatives. The obtained results are compared in terms of the enantiomeric separation achieved and mass spectrometric response. Linearity studies and the measurement of the limit of detection (LOD) show that the proposed method is suitable for a quantitative determination of enantiomers of several amino acids. The use of the programmed temperature vaporiser (PTV) technique for the injection of the untreated reaction mixture is a promising method for avoiding manual treatment of the sample and decreasing the LOD. KEY WORDS: chirality; amino acids; derivatization; GC-MS; in-situ analysis; planetary explorationThe in-situ search for organic molecules in extraterrestrial environments has been proposed for a better understanding of the solar system origin and the emergence of life on Earth. With this aim, detection of chemical biomarkers, i.e., of organic molecules that play an important role in biochemistry, will be one of the main goals of future space missions. Among the key chemical biomarkers on Earth, 1-3 amino and carboxylic acids which have been synthesized by experimental simulations under plausible prebiotic conditions, 4-6 have been detected in several meteorites 7-13 and in the lunar soil. 14-16 Thus, these chemical species appear to be widespread in the solar system, but they can exist without the presence of life. For this reason, the analysis of their optical activity seems to be a good complementary diagnostic tool to identify the link to a biotic or a prebiotic activity. In fact, almost exclusively L-amino acids are incorporated into proteins during microbial biosynthesis, although various D-amino acids have been found in archaea, yeasts, fungi, plants, insects, mollusks, and other eucaryotic organisms. [17][18][19] Because there are no evident biochemical reasons why L-amino acids should be selected over D-amino acids, it is generally assumed that life elsewhere could be based on either L-or D-amino acids, but not both. [20][21][22] Identifying an excess of D-amino acids in an extraterrestrial sample could provide unambiguous evidence for life that evolves independently from the Earth. [23][24] I...

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“…Amino acids have been observed in a number of carbonaceous chondrite meteorites of different classes. Thus the study of the origin and distribution of extraterrestrial amino acids has been the focus of several research studies (Kvenvolden et al 1970;Cronin & Moore 1971;Cronin & Pizzarello 1983;Pizzarello et al 1991;Ehrenfreund et al 2001b;Glavin et al 2006;Elsila et al 2007).…”

Section: Introductionmentioning

confidence: 99%

Quantum-chemical approach to serine formation in the interstellar medium: A possible reaction pathway

Singh

Gupta

Misra

et al. 2014

A&A

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Radical-radical and radical-neutral interaction schemes are very important for the formation of comparatively complex molecules in low-temperature chemistry. The formation of amino acids, such as serine, in the interstellar medium is quite difficult. We explored the possibility of serine formation in the interstellar medium through detected interstellar molecules such as CH, CO, and OH by radicalradical and radical-neutral interactions in the gaseous phase using rigorous quantum-chemical calculations. The reaction energies, the low potential barrier and the structures of all the geometries involved in the reaction path show that serine formation is possible in interstellar space via the reaction paths.

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Amino Acid Analyses of the Murchison, Murray, and Allende Carbonaceous Chondrites

Cited by 219 publications

References 10 publications

Prebiotic Synthesis of Hydrophobic and Protein Amino Acids

Prebiotic Synthesis of Hydrophobic and Protein Amino Acids

GC‐MS analysis of amino acid enantiomers as their N(O,S)‐perfluoroacyl perfluoroalkyl esters: Application to space analysis

Quantum-chemical approach to serine formation in the interstellar medium: A possible reaction pathway

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