Search for evidence of life in space: Analysis of enantiomeric organic molecules by N,N-dimethylformamide dimethylacetal derivative dependant Gas Chromatography–Mass Spectrometry

Freissinet, Caroline; Buch, Arnaud; Sternberg, R.; Szopa, Cyril; Geffroy-Rodier, Claude; Jelinek, Christine; Stambouli, Moncef

doi:10.1016/j.chroma.2009.11.009

Cited by 52 publications

(35 citation statements)

References 33 publications

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“…S.2a). However, the strength of DMF-DMA lies in its suitability for the analysis of chiral functional molecules (e.g., amino acids), when using it together with an enantioselective column (Freissinet et al, 2010) which was not part of this study.…”

Section: 22mentioning

confidence: 99%

Investigating the Effect of Perchlorate on Flight-like Gas Chromatography–Mass Spectrometry as Performed by MOMA on board the ExoMars 2020 Rover

et al. 2019

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The Mars Organic Molecule Analyzer (MOMA) instrument on board ESA's ExoMars 2020 rover will be essential in the search for organic matter. MOMA applies gas chromatography-mass spectrometry (GC-MS) techniques that rely on thermal volatilization. Problematically, perchlorates and chlorates in martian soils and rocks become highly reactive during heating (>200°C) and can lead to oxidation and chlorination of organic compounds, potentially rendering them unidentifiable. Here, we analyzed a synthetic sample (alkanols and alkanoic acids on silica gel) and a Silurian chert with and without Mg-perchlorate to evaluate the applicability of MOMA-like GC-MS techniques to different sample types and assess the impact of perchlorate. We used a MOMA flight analog system coupled to a commercial GC-MS to perform MOMA-like pyrolysis, in situ derivatization, and in situ thermochemolysis. We show that pyrolysis can provide a sufficient overview of the organic inventory but is strongly affected by the presence of perchlorates. In situ derivatization facilitates the identification of functionalized organics but showed low efficiency for n-alkanoic acids. Thermochemolysis is shown to be an effective technique for the identification of both refractory and functional compounds. Most importantly, this technique was barely affected by perchlorates. Therefore, MOMA GC-MS analyses of martian surface/subsurface material may be less affected by perchlorates than commonly thought, in particular when applying the full range of available MOMA GC-MS techniques.

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Section: 22mentioning

confidence: 99%

Investigating the Effect of Perchlorate on Flight-like Gas Chromatography–Mass Spectrometry as Performed by MOMA on board the ExoMars 2020 Rover

et al. 2019

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“…Unfortunately, the selected derivatization technique is unsuitable for evaluating quantitative differences of the enantiomers of amino acids, because it induces racemisation of the analytes. By now several derivatization techniques including DMF‐DMA and the reaction with hexafluoroacetone have been developed and validated for the in situ analysis on extraterrestrial samples on Mars.…”

Section: Enantioselective Chromatography and Space Missionsmentioning

confidence: 99%

“…vibrations, radiation by photons and/or energetic particles, space vacuum, and large temperature range do not alter the separation efficiency and chiral selectivity of the Chirasil‐β‐Dex column . Therefore it is exclusively applied as CSP onboard of the current MSL mission as well as on the payload of the future Exo‐Mars mission – a joint collaboration of the ESA and the Russian Federal Space Agency (Roskosmos) ,…”

Section: Enantioselective Chromatography and Space Missionsmentioning

confidence: 99%

Enantioselective Gas Chromatography in Search of the Origin of Biomolecular Asymmetry in Outer Space

Myrgorodska

Javelle

Meinert

et al. 2016

Israel Journal of Chemistry

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Since the pioneering work of Emanuel Gil‐Av and his associates at the Weizmann Institute of Science the direct gas chromatographic resolution of enantiomers has found its application in different fields of natural sciences, even expanding to space research and astrobiology. In these domains the resolution of chiral molecules of prebiotic relevance is of particular interest, since the determination of ratios between l‐ and d‐enantiomers within non‐terrestrial samples is assumed to shed light on the origin of biomolecular homochirality and the beginnings of life itself. According to an astrophysical scenario, the first molecular symmetry breaking event occurred upon irradiation of chiral organic molecules with circularly polarized light present in the interstellar medium. To examine this hypothesis, among others, chiral gas chromatographic stationary phases have been widely used to provide the differentiation of enantiomers in extracts of meteorites, samples of simulated interstellar ices and Mars soil analogues. Moreover several chiral capillary columns have been selected for in situ analyses of extraterrestrial organic matter by Mars missions and the cometary Rosetta mission. This review will highlight current advances of enantioselective gas chromatography applied to space science.

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“…Probenbohr‐ und Probenverteilungssystem extrahieren zunächst Stichproben, die organische Komponenten werden dann wahlweise in zwei Pyrolyseöfen mit 600 °C und 180 °C in die Gasphase überführt. Hydroxycarbonsäuren und zwitterionische Aminosäuren überführt ein einstufiger Derivatisierungsschritt in flüchtige Derivate, und zwar durch Reaktion mit N,N‐Dimethylformamid/O,O‐Dimethylacetal (DMF‐DMA, Abbildung 7) 25,26,31. Die Enantiomere quantitativ zu trennen, gelingt jedoch nur für Valin, Isoleucin, Asparaginsäure und Phenylalanin.…”

Section: Enantiomerenanalytik Im Allunclassified

“…Polymeres Chirasil‐β‐Dex (Abbildung 2, rechts, S. 661) gilt als optimale CSP, um auf dem Mars nach Homochiralität zu suchen. Deshalb wird ausschließlich diese CSP für die laufende Mars‐Science‐Laboratory(MSL)‐Mission und die kommenden Exo‐Mars‐Missionen eingesetzt 31,34. Chirasil‐β‐Dex behält die volle Trennleistung und Chiralitätserkennung unter den Strahlungsbedingungen, wie sie im Weltraum vorherrschen 35…”

Section: Mars‐missionen Mit Gaschromatographenunclassified

Effect of Stereochemistry of Avermectin‐Like 6,6‐Spiroketals on Biological Activities and Endogenous Biotransformations in Streptomyces avermectinius

et al. 2014

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Natural avermectins (AVEs) share a 6,6-spiroketal moiety with an exclusive R configuration at the C21 spirocyclic junction. Herein, we report the characterization of nine AVE-like spiroketals of two types (C21 S and R) in a mutant strain that lacks spirocyclase activity. Comparative analysis of their structures facilitated evaluation of the effect of stereochemistry on endogenous biotransformations and biological activities of the spiroketals.

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Search for evidence of life in space: Analysis of enantiomeric organic molecules by N,N-dimethylformamide dimethylacetal derivative dependant Gas Chromatography–Mass Spectrometry

Cited by 52 publications

References 33 publications

Investigating the Effect of Perchlorate on Flight-like Gas Chromatography–Mass Spectrometry as Performed by MOMA on board the ExoMars 2020 Rover

Investigating the Effect of Perchlorate on Flight-like Gas Chromatography–Mass Spectrometry as Performed by MOMA on board the ExoMars 2020 Rover

Enantioselective Gas Chromatography in Search of the Origin of Biomolecular Asymmetry in Outer Space

Effect of Stereochemistry of Avermectin‐Like 6,6‐Spiroketals on Biological Activities and Endogenous Biotransformations in Streptomyces avermectinius

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