Papers by Uwe Meierhenrich
Advances in Astrobiology and Biogeophysics
Topics in Current Chemistry, 2012
In Sect. 5.3, the second paragraph should read [. . .] Kondepudi et al. [112, 113] have establish... more In Sect. 5.3, the second paragraph should read [. . .] Kondepudi et al. [112, 113] have established this concept within a number of autocatalytic systems to demonstrate its effectiveness (Fig. 9). The reductive Zn-mediated alkylation reported by Soai et al. in 1995 was the first truly autocatalytic asymmetric amplification, with greater than 99.5% ee observed [114]. Both Breslow [115] and Blackmond [116, 117] have reported successful enantiomeric enhancements of amino acids in the context of asymmetric amplification. One study describes an ee amplification achieved via the conversion of one enantiomer to the other under racemizing conditions [118].
Nachrichten aus der Chemie, 2002
ABSTRACT
Nachrichten aus der Chemie, 2002
ABSTRACT
Science (New York, N.Y.), Jan 31, 2015
Comets harbor the most pristine material in our solar system in the form of ice, dust, silicates,... more Comets harbor the most pristine material in our solar system in the form of ice, dust, silicates, and refractory organic material with some interstellar heritage. The evolved gas analyzer Cometary Sampling and Composition (COSAC) experiment aboard Rosetta's Philae lander was designed for in situ analysis of organic molecules on comet 67P/Churyumov-Gerasimenko. Twenty-five minutes after Philae's initial comet touchdown, the COSAC mass spectrometer took a spectrum in sniffing mode, which displayed a suite of 16 organic compounds, including many nitrogen-bearing species but no sulfur-bearing species, and four compounds-methyl isocyanate, acetone, propionaldehyde, and acetamide-that had not previously been reported in comets.
Life
Homochiral proteins orchestrate biological functions throughout all domains of life, but the orig... more Homochiral proteins orchestrate biological functions throughout all domains of life, but the origin of the uniform l-stereochemistry of amino acids remains unknown. Here, we describe enantioselective adsorption experiments of racemic alanine and leucine onto homochiral d- and l-quartz as a possible mechanism for the abiotic emergence of biological homochirality. Substantial racemate resolution with enantiomeric excesses of up to 55% are demonstrated to potentially occur in interstitial pores, along grain boundaries or small fractures in local quartz-bearing environments. Our previous hypothesis on the enhanced enantioselectivity due to uranium-induced fission tracks could not be validated. Such capillary tubes in the near-surface structure of quartz have been proposed to increase the overall chromatographic separation of enantiomers, but no systematic positive correlation of accumulated radiation damage and enantioselective adsorption was observed in this study. In general, the natu...
Symmetry
Acyclic saturated hydrocarbon enantiomers were resolved by gas chromatography using a β-cyclodext... more Acyclic saturated hydrocarbon enantiomers were resolved by gas chromatography using a β-cyclodextrin-based chiral stationary phase. The stereospecific synthesis of single enantiomers of 4-methyloctane allowed to assign the absolute stereochemical configuration to the resolved enantiomers. Data show that the (S)-4-methyloctane shows higher chromatographic retention as compared to the (R)-4-methyloctane due to stronger van der Waals interactions with the β-cyclodextrin chiral selector. This introductive research presents future prospects for the separation of stereoisomers of larger branched hydrocarbons. We discuss the importance of chiral hydrocarbons, more precisely the stereochemistry of the isoprenoid alkanes pristane and phytane, as potential biosignatures stable on geological timescales. The origins of pristane and phytane in Earth sediments are presented, and we detail the implications for the search of extinct or extant life on Mars. The data presented here will help to syste...
Encyclopedia of Astrobiology
Life
The biomolecular homochirality in living organisms has been investigated for decades, but its ori... more 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 synthe...
Astrobiology
The second ExoMars mission will be launched in 2020 to target an ancient location interpreted to ... more The second ExoMars mission will be launched in 2020 to target an ancient location interpreted to have strong potential for past habitability and for preserving physical and chemical biosignatures (as well as abiotic/prebiotic organics). The mission will deliver a lander with instruments for atmospheric and geophysical investigations and a rover tasked with searching for signs of extinct life. The ExoMars rover will be equipped with a drill to collect material from outcrops and at depth down to 2 m. This subsurface sampling capability will provide the best chance yet to gain access to chemical biosignatures. Using the powerful Pasteur payload instruments, the ExoMars science team will conduct a holistic search for traces of life and seek corroborating geological context information.
Science (New York, N.Y.), Jan 13, 2017
We detected ribose and related sugars in the organic residues of simulated interstellar ices usin... more We detected ribose and related sugars in the organic residues of simulated interstellar ices using multidimensional gas chromatography. Kawai questions the formation of sugar compounds in the ices and suggests that they arise from a classical formose reaction during sample workup for analysis. We disagree with this hypothesis and present additional data to argue that Kawai's criticism does not apply.
Journal of Natural Products, 2017
Angewandte Chemie, 2016
Frankincense (olibanum) is one of the oldest aromatic materials used by humans, but the key molec... more Frankincense (olibanum) is one of the oldest aromatic materials used by humans, but the key molecular constituents contributing to its characteristic odor remained unknown. Reported herein is the discovery that (1S,2S)-(+)-trans- and (1S,2R)-(+)-cis-2-octylcyclopropyl-1-carboxylic acids are highly potent and substantive odorants occurring in ppm amounts in all of the frankincense samples analyzed, even those showing radically different volatile compositions. These cyclopropyl-derived acids provide the very characteristic old churchlike endnote of the frankincense odor.
Science, 2016
Making ribose in interstellar ices Astrobiologists have long speculated on the origin of prebioti... more Making ribose in interstellar ices Astrobiologists have long speculated on the origin of prebiotic molecules such as amino acids and sugars. Meinert et al. demonstrated that numerous prebiotic molecules can be formed in an interstellar-analog sample containing a mixture of simple ices of water, methanol, and ammonia. They irradiated the sample with ultraviolet light under conditions similar to those expected during the formation of the solar system. This yielded a wide variety of sugars, including ribose—a major constituent of ribonucleic acid (RNA). Science , this issue p. 208
Exo Astro Biology, Jul 30, 2001
Physical chemistry chemical physics : PCCP, May 20, 2016
Photoelectron circular dichroism (PECD) manifests itself as an intense forward/backward asymmetry... more Photoelectron circular dichroism (PECD) manifests itself as an intense forward/backward asymmetry in the angular distribution of photoelectrons produced from randomly-oriented enantiomers by photoionization with circularly-polarized light (CPL). As a sensitive probe of both photoionization dynamics and of the chiral molecular potential, PECD attracts much interest especially with the recent performance of related experiments with visible and VUV laser sources. Here we report, by use of quasi-perfect CPL VUV synchrotron radiation and using a double imaging photoelectron/photoion coincidence (i(2)PEPICO) spectrometer, new and very accurate values of the corresponding asymmetries on showcase chiral isomers: camphor and fenchone. These data have additionally been normalized to the absolute enantiopurity of the sample as measured by a chromatographic technique. They can therefore be used as benchmarking data for new PECD experiments, as well as for theoretical models. In particular we fo...
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Papers by Uwe Meierhenrich