Quantitative enantioseparation of amino acids by comprehensive two-dimensional gas chromatography applied to non-terrestrial samples

Myrgorodska, Iuliia; Meinert, Cornelia; Martins, Zita; d’Hendecourt, Louis Le Sergeant; Meierhenrich, Uwe J.

doi:10.1016/j.chroma.2016.01.014

Cited by 40 publications

(26 citation statements)

References 26 publications

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“…For OPA/NAC, the reaction between chiral amino acids and the chiral thiol N-acetyl- l -cysteine produces two diastereomers (representing the two amino acid enantiomers) (Scheme 2, panel B) which can be separated using non-chiral reversed phase LC columns. Other methodologies used for chiral separation of meteoritic amino acids include the use of enantioselective chiral columns for GC analysis of N -ethoxycarbonyl ethyl ester (ECEE) and N -ethoxycarbonyl heptafluorobutyl ester (ECHFBE) derivatives [94,95], GC analysis of amino acids as n -pentafluoropropionic anhydride (PFP) alkyl ester diastereomers [96,97,98], and the use of a chiral zwitterionic surfactant for micellar electrokinetic chromatography of Pacific Blue succinimidyl ester (PBSE) derivatives [99]. Further details regarding both enantiomeric and stable isotopic analyses of meteoritic amino acids are reviewed in the literature (e.g., [91,100,101,102,103,104]).…”

Section: Analysis Of Extraterrestrial Organic Compounds: Methods Ovmentioning

confidence: 99%

“…Likewise, some unknown meteoritic organics are potentially masked by chromatographic co-elutions in conventional one-dimensional chromatography approaches. For example, glutamic acid and pyroglutamic acid are known to coelute with one another when implementing one-dimensional GC, but can be resolved when using novel two-dimensional GC×GC techniques [95].…”

Section: Analysis Of Extraterrestrial Organic Compounds: Methods Ovmentioning

confidence: 99%

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Methodologies for Analyzing Soluble Organic Compounds in Extraterrestrial Samples: Amino Acids, Amines, Monocarboxylic Acids, Aldehydes, and Ketones

Simkus

Aponte

Elsila

et al. 2019

Life

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Soluble organic compositions of extraterrestrial samples offer valuable insights into the prebiotic organic chemistry of the solar system. This review provides a summary of the techniques commonly used for analyzing amino acids, amines, monocarboxylic acids, aldehydes, and ketones in extraterrestrial samples. Here, we discuss possible effects of various experimental factors (e.g., extraction protocols, derivatization methods, and chromatographic techniques) in order to highlight potential influences on the results obtained from different methodologies. This detailed summary and assessment of current techniques is intended to serve as a basic guide for selecting methodologies for soluble organic analyses and to emphasize some key considerations for future method development.

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Section: Analysis Of Extraterrestrial Organic Compounds: Methods Ovmentioning

confidence: 99%

Section: Analysis Of Extraterrestrial Organic Compounds: Methods Ovmentioning

confidence: 99%

Methodologies for Analyzing Soluble Organic Compounds in Extraterrestrial Samples: Amino Acids, Amines, Monocarboxylic Acids, Aldehydes, and Ketones

Simkus

Aponte

Elsila

et al. 2019

Life

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“…A multidimensional gas chromatography method for the separation and quantification of non-racemic samples of amino acids has been developed and extended to the detection and quantification of non-proteinogenic amino acids in extraterrestrial samples [69,70]. Prior to the analysis of an acid-hydrolyzed extract of the Murchison meteorite by enantioselective two-dimensional gas chromatography coupled to a time-of-flight mass spectrometer (GC × GC-TOFMS), the amino acids were transformed into their N ( O , S ) - ethoxycarbonylheptafluorobutyl-corresponding esters.…”

Section: Amino Acidsmentioning

confidence: 99%

The Astrophysical Formation of Asymmetric Molecules and the Emergence of a Chiral Bias

Garcia

Meinert

Sugahara

et al. 2019

Life

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The biomolecular homochirality in living organisms has been investigated for decades, but its origin remains poorly understood. It has been shown that circular polarized light (CPL) and other energy sources are capable of inducing small enantiomeric excesses (ees) in some primary biomolecules, such as amino acids or sugars. Since the first findings of amino acids in carbonaceous meteorites, a scenario in which essential chiral biomolecules originate in space and are delivered by celestial bodies has arisen. Numerous studies have thus focused on their detection, identification, and enantiomeric excess calculations in extraterrestrial matrices. In this review we summarize the discoveries in amino acids, sugars, and organophosphorus compounds in meteorites, comets, and laboratory-simulated interstellar ices. Based on available analytical data, we also discuss their interactions with CPL in the ultraviolet (UV) and vacuum ultraviolet (VUV) regions, their abiotic chiral or achiral synthesis, and their enantiomeric distribution. Without doubt, further laboratory investigations and upcoming space missions are required to shed more light on our potential extraterrestrial molecular origins.

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“…More than ninety different amino acids, which represent a nearly complete structural diversity, have been identified from carbonaceous chondrites. The diversity of organics provides insight into the chemical nature of the meteorite parent bodies, [2][3][4] however although meteoritic amino acids have been studied for over 60 years using a variety of techniques, [5][6][7][8][9][10] their synthetic origins remain a subject of debate. 11 Accurately measuring the molecular distributions of organic compounds and comparing the relative abundances of different compound types is key for understanding the effects of aqueous and thermal processing inside the parent body and the synthetic relationships between various classes of meteoritic organic compounds.…”

Section: Introductionmentioning

confidence: 99%

Analyses of Aliphatic Aldehydes and Ketones in Carbonaceous Chondrites

Aponte

Whitaker

Powner

et al. 2019

ACS Earth Space Chem.

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Aliphatic aldehydes and ketones are essential building blocks for the synthesis of more complex organic compounds. In spite of their potentially key role as precursors of astrobiologically-important molecules, such as amino acids and carboxylic acids, this family of compounds has scarcely been evaluated in carbonaceous chondrites. The paucity of such analyses likely derives from the low concentration of aldehydes and ketones in the meteorites, and from the currently used chromatographic methodologies that have not been optimized for meteorite analysis. In this work, we report the development of a novel analytical method to quantify the molecular distribution and compound-specific isotopic analysis of 29 aliphatic aldehydes and ketones. Using this method, we have investigated the molecular distribution and 13 C-isotopic composition of aldehydes and ketones in ten carbonaceous chondrites from the CI, CM, CR and CV groups. The total concentration of carbonyl compounds ranged from 130 to 1000 nmolg-1 of meteorite, with formaldehyde, acetaldehyde, and acetone being the most abundant species in all investigated samples. The 13 C-isotopic values ranged from-67 to +64‰ and we did not observe clear relationships between 13 C-content and molecular weight. Accurately measuring the relative abundances, determining the molecular distribution, and isotopic composition of chondritic organic compounds is central in assessing both their formation chemistry and synthetic relationships.

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Quantitative enantioseparation of amino acids by comprehensive two-dimensional gas chromatography applied to non-terrestrial samples

Cited by 40 publications

References 26 publications

Methodologies for Analyzing Soluble Organic Compounds in Extraterrestrial Samples: Amino Acids, Amines, Monocarboxylic Acids, Aldehydes, and Ketones

Methodologies for Analyzing Soluble Organic Compounds in Extraterrestrial Samples: Amino Acids, Amines, Monocarboxylic Acids, Aldehydes, and Ketones

The Astrophysical Formation of Asymmetric Molecules and the Emergence of a Chiral Bias

Analyses of Aliphatic Aldehydes and Ketones in Carbonaceous Chondrites

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