Two homologous series of alkylpyridines in the Murchison meteorite

Yamashita, Yohei; Naraoka, Hiroshi

doi:10.2343/geochemj.2.0340

Cited by 27 publications

(34 citation statements)

References 26 publications

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Section: Resultsmentioning

confidence: 99%

“…The spatial distributions were not the same among the homologues. The compounds belonging to the C n H m N + and C n H m N 2 + homologues were probably synthesized and evolved by various chemical pathways, including dehydration, oxidation, or reduction (Yamashita and Naraoka 2014;Naraoka et al 2017). The different spatial resolutions of the various members of the C n H 2n-1 N 2 + homologues might be due to the spatial distributions of the different isomers resulting from the fact that they were generated via different synthetic pathways.…”

Section: Spatial Distributions Of the C N H 2n-1 N 2 + And C N H 2n Nmentioning

confidence: 99%

“…The FT-ICR/MS analysis also revealed presence of metalorganic compounds in various meteorites, including the Murchison meteorite (Ruf et al 2017). In a more recent study, more than 600 peaks due to the presence of alkylated homologues of N-containing heterocyclic compounds, which are mainly comprised of alkylimidazole and alkylpyridine, were identified by HPLC coupled with HRMS using Orbitrap MS in an MeOH extract obtained from the Murchison meteorite (Yamashita and Naraoka 2014;Naraoka et al 2017). These studies suggested that the CHN compounds may have been synthesized and evolved during in situ H 2 generation via the aqueous alteration of meteoritic anhydrous silicates.…”

Section: Introductionmentioning

confidence: 95%

“…). In a more recent study, more than 600 peaks due to the presence of alkylated homologues of N‐containing heterocyclic compounds, which are mainly comprised of alkylimidazole and alkylpyridine, were identified by HPLC coupled with HRMS using Orbitrap MS in an MeOH extract obtained from the Murchison meteorite (Yamashita and Naraoka ; Naraoka et al. ).…”

Section: Introductionmentioning

confidence: 99%

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High‐mass resolution molecular imaging of organic compounds on the surface of Murchison meteorite

Hashiguchi

Naraoka

2018

Meteorit & Planetary Scien

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High‐resolution mass spectrometry (HRMS) imaging by desorption electrospray ionization (DESI) coupled with Orbitrap MS using methanol (MeOH) spray was performed on a fragment of the Murchison (CM2) meteorite in this study. Homologues of CnH2n–1N2+ (n = 7–9) and CnH2nNO+ (n = 9–14) were detected on the sample surface by the imaging. A high‐performance liquid chromatography (HPLC)/HRMS analysis of MeOH extracts from the sample surface after DESI/HRMS imaging indicated that the CnH2n–1N2+ homologues corresponds to alkylimidazole, and that a few isomers of the CnH2nNO+ homologues present in the sample. The alkylimidazoles and CnH2nNO+ homologues displayed different spatial distributions on the surface of the Murchison fragment, indicating chromatographic separation effects during aqueous alteration. Moreover, the distribution pattern of compounds is also different among homologues. This is probably also resulting from the separation of isomers by similar chromatographic effects, or different synthetic pathways. Alkylimidazoles and the CnH2nNO+ homologues are mainly distributed in the matrix region of the Murchison by mineralogical observations, which is consistent with previous reports. Altered minerals (e.g., Fe‐oxide, Fe‐sulfide, and carbonates) occurred in this region. However, no clear relationship was found between these minerals and the organic compounds detected by DESI/HRMS imaging. Although this result might be due to scale differences between the spatial resolution of DESI/HRMS imaging and the grain size in the matrix of the Murchison, our results would indicate that alkylimidazoles and the CnH2nNO+ homologues in the Murchison fragment were mainly synthesized by different processes from hydrothermal alteration on the parent body.

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Section: Resultsmentioning

confidence: 99%

Section: Spatial Distributions Of the C N H 2n-1 N 2 + And C N H 2n Nmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

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High‐mass resolution molecular imaging of organic compounds on the surface of Murchison meteorite

Hashiguchi

Naraoka

2018

Meteorit & Planetary Scien

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“…Yamashita and Naraoka (2014) report two homologous series of alkylpyridines (C n H 2n-5 N and C n H 2n-7 N) identified in the methanol extract of the Murchison meteorite by liquid chromatography/high-resolution mass spectrometry. The organic components consisting of C, H, and N are likely to have escaped chemical oxidation during parent body alteration and may thus record the early stage of formation of meteoritic organic components.…”

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confidence: 99%

Preface: Evolution of refractory grains, volatiles, and organic molecules from the interstellar medium to the early solar system

2014

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Primitive extraterrestrial materials record the early evolution of the solar system that predated planet formation. They also preserve the interstellar heritage from prior to the Sun's birth in the form of presolar grains and potentially as isotopic signatures of light elements in organic matter and specific molecules. It is one of the key issues in cosmochemistry to link the birth and evolution of the solar system to the evolution of the interstellar medium (ISM) and the Galaxy. To address this issue, an interdisciplinary approach linking analysis of extraterrestrial materials including samples returned by spacecraft, laboratory experiments, astronomical observations, and theoretical studies is crucial.This special issue arose from a session "Refractory Grains, Volatiles, and Organic Molecules Inherited from the Interstellar Medium" at the Goldschmidt Conference (Aug. 25-30, 2013, Florence Italy) and consists of six articles covering a wide array of topics and disciplines to explore various perspectives of cosmochemistry; astronomical observation, laboratory experiments, extraterrestrial organic chemistry, astrophysical modeling, in-situ isotopic analyses, chronology, and sample-return mission. Dartois et al. (2014) summarize observational and laboratory studies on interstellar carbonaceous dust to explore the link between ISM carbonaceous dust and insoluble organic matter (IOM) found in chondrites and interplanetary dust particles (IDPs). Several forms of carbonaceous solids are observed in the ISM (polyaromatic hydrocarbons (PAHs), amorphous carbons, hydrogenated amorphous carbons (a-C:H), fullerenes, and ices that further turn into macromolecular organic residues after ice-sublimation), among which PAHs, a-C:H and/or macromolecular organic residues would be the main precursor of solar system carbonaceous materials. PAHs and a-C:H are more aromatic and contain less oxygen and nitrogen than solar-system IOM. Organic matter formed by photolysis and/or radiolysis of ice in laboratories do not match the entire infrared spectral features of IOMs either. These lines of evidences indicate that further evolution of organic materials may have occurred in the early stage of solar-system formation from ISM carbonaceous dust as a precursor.The evolution of organic matter in the early solar system may also be recorded in soluble organic components extracted from primitive meteorites. Yamashita and Naraoka (2014) report two homologous series of alkylpyridines (C n H 2n-5 N and C n H 2n-7 N) identified in the methanol extract of the Murchison meteorite by liquid chromatography/high-resolution mass spectrometry. The organic components consisting of C, H, and N are likely to have escaped chemical oxidation during parent body alteration and may thus record the early stage of formation of meteoritic organic components. Laboratory simulation experiments involving HCHO, CH 3 CHO, and NH 3 produced alkylpyridines, which provided a plausible synthetic pathway for meteoritic alkylpyridines via aldol condensation and Chichibabin-typ...

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In situ organic compound analysis on a meteorite surface by desorption electrospray ionization coupled with an Orbitrap mass spectrometer

Naraoka

Hashiguchi

2018

Rapid Comm Mass Spectrometry

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Two homologous series of alkylpyridines in the Murchison meteorite

Cited by 27 publications

References 26 publications

High‐mass resolution molecular imaging of organic compounds on the surface of Murchison meteorite

High‐mass resolution molecular imaging of organic compounds on the surface of Murchison meteorite

Preface: Evolution of refractory grains, volatiles, and organic molecules from the interstellar medium to the early solar system

In situ organic compound analysis on a meteorite surface by desorption electrospray ionization coupled with an Orbitrap mass spectrometer

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