Die umfassende zweidimensionale Gaschromatographie – eine neue Dimension für analytische Trennwissenschaften

Meinert, Cornelia; Meierhenrich, Uwe J.

doi:10.1002/ange.201200842

Cited by 9 publications

(3 citation statements)

References 154 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A major challenge of our research is to shed some light on the asymmetric mechanism for the formation of chiral prebiotic molecules based on their interaction with UV-CPL as an external chiral force with particular emphasis on absolute asymmetric photolysis and synthesis. Therefore, we are identifying various chiral organic molecules and quantifying any small ee in carbonaceous chondrites by using the highly increased resolution power of novel multidimensional gas chromatography coupled to time-of-flight mass spectrometry (GC×GC-TOFMS) [4]. Detected ees are compared with those produced under controlled asymmetric photolysis experiments using circularly polarized synchrotron radiation (CPSR) at the synchrotron radiation source SOLEIL (France).…”

Section: How Did Life Originate?mentioning

confidence: 99%

The origin of biomolecular asymmetry – Insights from cometary and meteoritic matter

Meinert

Meierhenrich

Nahon

et al. 2014

BIO Web of Conferences

View full text Add to dashboard Cite

Abstract. The chemistry of life is purely stereospecific. The fundamental biopolymers -proteins and nucleic acids -are intrinsically chiral due to their molecular building blocks, namely L-amino acids and D-sugars. Hypotheses for the evolutionary origin of that strict stereochemical selection include the asymmetric photochemistry model by which circularly polarized (CP) photons induced an enantiomeric excess in chiral organic molecules via asymmetric photolysis. The transfer of a distinct chirality from chiral photons to organic molecules is assumed to have occurred in environments of interstellar molecular clouds. This model is strengthened by the observation of CP light in the star-forming region of Orion. Due to our laboratory experiments mimicking cometary ice evolution, we show that molecules of prebiotic interest such as amino and diamino acids are formed in inter/protostellar environments and might have been subjected to CP vacuum-UV radiation before and during their space journey to the early Earth. How did Life originate?The goal is to understand the scenarios by which extraterrestrial organic matter has seeded the surface of the primitive Earth and propose an astrophysical explanation for the origin of asymmetry in chiral protein and nucleotide precursors that may have led later to homochirality an assumed prerequisite for Life on Earth [1].Why were left-handed amino acids selected for its architecture? Topical research reasons that circularly polarized light (CPL) -observed in star-forming regions -might induce an enantiomeric excess (ee) in chiral organic molecules via asymmetric interstellar photon-molecule interactions [2,3]. A major challenge of our research is to shed some light on the asymmetric mechanism for the formation of chiral prebiotic molecules based on their interaction with UV-CPL as an external chiral force with particular emphasis on absolute asymmetric photolysis and synthesis. Therefore, we are identifying various chiral organic molecules and quantifying any small ee in carbonaceous chondrites by using the highly increased resolution power of novel multidimensional gas chromatography coupled to time-of-flight mass spectrometry (GC×GC-TOFMS) [4]. Detected ees are compared with those produced under controlled asymmetric photolysis experiments using circularly polarized synchrotron radiation (CPSR) at the synchrotron radiation source SOLEIL (France). First promising

show abstract

Section: How Did Life Originate?mentioning

confidence: 99%

The origin of biomolecular asymmetry – Insights from cometary and meteoritic matter

Meinert

Meierhenrich

Nahon

et al. 2014

BIO Web of Conferences

View full text Add to dashboard Cite

show abstract

“…The coupling of comprehensive two-dimensional gas chromatography with mass spectrometry as the “third dimension” also provides important information for substance identification. The combination of these advantages makes the GC×GC one of the most powerful separation methods for the chemical analysis of organic compounds in complex matrices [14]. The efficiency of this modern analysis technology has recently been demonstrated using different types of wine in nontarget screenings [15–17].…”

Section: Introductionmentioning

confidence: 99%

Analysis of sesquiterpene hydrocarbons in grape berry exocarp (Vitis vinifera L.) using in vivo-labeling and comprehensive two-dimensional gas chromatography–mass spectrometry (GC×GC–MS)

Könen¹,

Wüst²

2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Sesquiterpenes are structurally diverse, potent flavoring substances that significantly influence the aroma profile of grapes (Vitis vinifera L.) at the time of physiological ripening. To investigate these natural compounds, freshly harvested, ripe berries of the red wine variety Lemberger (Vitis vinifera subsp. vinifera L.) were analyzed using comprehensive two-dimensional gas chromatography (GC×GC) coupled to a time-of-flight mass spectrometer (TOF–MS) after headspace-solid phase microextraction (HS-SPME). The identification of structurally complex natural compounds, such as sesquiterpenes from fruits and vegetables, is often reported as “tentative”, as authentic standards are not commercially available for most of the analytes. For this reason, feeding experiments (in vivo labeling) were carried out using the stable isotope-labeled precursors [5,5-2H2]-1-deoxy-ᴅ-xylulose (d 2-DOX) and [6,6,6-2H3]-(±)-mevalonolactone (d 3-MVL) to clearly identify the volatiles. Based on the recorded mass spectra of the unlabeled and deuterated compounds, mechanisms for sesquiterpene formation in V. vinifera could be proposed and already known pathways could be confirmed or disproved. For example, the HS-SPME–GC×GC–TOF–MS measurements of fed sample material showed that the tricyclic sesquiterpene hydrocarbons α-copaene, β-copaene, α-cubebene, β-cubebene and the bicyclic δ-cadinene were biosynthesized via (S)-(−)-germacrene D rather than via (R)-(+)-germacrene D as intermediate.

show abstract

“…[20] Further important improvement of gas chromatographic resolution of amino acid enantiomers has been achieved as a result of the development of multidimensional gas chromatography (GC GC) techniques. [21] The first enantioselective two-dimensional GC with valveless switching dates back to 1983 when the efficient separation of amino acids was demonstrated. [22] Nowadays, the Chirasil-Val stationary phase is often used in the first chromatographic dimension for the enantioselective resolution of different amino acid derivatives.…”

mentioning

confidence: 99%

Derivatization and Multidimensional Gas‐Chromatographic Resolution of α‐Alkyl and α‐Dialkyl Amino Acid Enantiomers

Meinert

Meierhenrich

2014

ChemPlusChem

Self Cite

View full text Add to dashboard Cite

Dedicated to Professor Martin Quack on the occasion of his 65th birthdayThe quantitative resolution of amino acid enantiomers is crucial to a number of fields of bioanalytical chemistry, including food and plant analysis, metabolomics, medicinal chemistry, and archeochemistry. The enantioselective analysis of a-dialkyl amino acids, however, has proven more difficult than for proteinaceous a-protonated amino acids. Herein, the development of an analytical method capable of base-line resolving enantiomers of a-alkyl and a-dialkyl amino acids in two chromatographic dimensions is reported. It was found that enantiomers of a-dialkyl amino acids can be readily resolved with the use of an enantioselective Chirasil-Val stationary phase in the first chromatographic dimension and a polyethylene glycol stationary phase in the second dimension. These data offer new possibilities for the enantioselective resolution and precise quantification of non-biological a-dialkyl amino acids. This methodology will subsequently be applied particularly towards enantioselective analyses of samples relevant for understanding of the origin of homochirality on Earth such as meteorites, comets, and interstellar ices.

show abstract

Die umfassende zweidimensionale Gaschromatographie – eine neue Dimension für analytische Trennwissenschaften

Cited by 9 publications

References 154 publications

The origin of biomolecular asymmetry – Insights from cometary and meteoritic matter

The origin of biomolecular asymmetry – Insights from cometary and meteoritic matter

Analysis of sesquiterpene hydrocarbons in grape berry exocarp (Vitis vinifera L.) using in vivo-labeling and comprehensive two-dimensional gas chromatography–mass spectrometry (GC×GC–MS)

Derivatization and Multidimensional Gas‐Chromatographic Resolution of α‐Alkyl and α‐Dialkyl Amino Acid Enantiomers

Contact Info

Product

Resources

About