Mechanochemical Prebiotic Peptide Bond Formation**

Stolar, Tomislav; Grubešić, Saša; Cindro, N.; Meštrović, Ernest; Užarević, Krunoslav; Hernández, José G.

doi:10.1002/anie.202100806

Cited by 39 publications

(30 citation statements)

References 84 publications

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“…and A.4. are only available in electronic form at the CDS via anonymous ftp to cdsarc.u-strasbg.fr (130.79.128.5) or via http://cdsweb.u-strasbg.fr/cgi-bin/qcat?J/A+A/ ciplines, including prebiotic astrochemistry (Ruiz-Mirazo et al 2014;Sandford et al 2020;Stolar et al 2021).…”

Section: Introductionmentioning

confidence: 99%

Laboratory rotational spectroscopy of acrylamide and a search for acrylamide and propionamide toward Sgr B2(N) with ALMA

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Koucký

et al. 2022

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Context. Numerous complex organic molecules have been detected in the universe and among them are amides, which are considered as prime models for species containing a peptide linkage. In its backbone, acrylamide (CH 2 CHC(O)NH 2 ) bears not only the peptide bond, but also the vinyl functional group that is a common structural feature in many interstellar compounds. This makes acrylamide an interesting candidate for searches in the interstellar medium. In addition, a tentative detection of the related molecule propionamide (C 2 H 5 C(O)NH 2 ) has been recently claimed toward Sgr B2(N). Aims. The aim of this work is to extend the knowledge of the laboratory rotational spectrum of acrylamide to higher frequencies, which would make it possible to conduct a rigorous search for interstellar signatures of this amide using millimeter wave astronomy. Methods. We measured and analyzed the rotational spectrum of acrylamide between 75 and 480 GHz. We searched for emission of acrylamide in the imaging spectral line survey ReMoCA performed with the Atacama Large Millimeter/submillimeter Array toward Sgr B2(N). We also searched for propionamide in the same source. The astronomical spectra were analyzed under the assumption of local thermodynamic equilibrium. Results. We report accurate laboratory measurements and analyses of thousands of rotational transitions in the ground state and two excited vibrational states of the most stable syn form of acrylamide. In addition, we report an extensive set of rotational transitions for the less stable skew conformer. Tunneling through a low energy barrier between two symmetrically equivalent configurations has been revealed for this higher-energy species. Neither acrylamide nor propionamide were detected toward the two main hot molecular cores of Sgr B2(N). We did not detect propionamide either toward a position located to the east of the main hot core, thereby undermining the recent claim of its interstellar detection toward this position. We find that acrylamide and propionamide are at least 26 and 14 times less abundant, respectively, than acetamide toward the main hot core Sgr B2(N1S), and at least 6 and 3 times less abundant, respectively, than acetamide toward the secondary hot core Sgr B2(N2). Conclusions. A comparison with results of astrochemical kinetics model for related species suggests that acrylamide may be a few hundred times less abundant than acetamide, corresponding to a value that is at least an order of magnitude lower than the observational upper limits. Propionamide may be as little as only a factor of two less abundant than the upper limit derived toward Sgr B2(N1S). Lastly, the spectroscopic data presented in this work will aid future searches of acrylamide in space.

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Section: Introductionmentioning

confidence: 99%

Laboratory rotational spectroscopy of acrylamide and a search for acrylamide and propionamide toward Sgr B2(N) with ALMA

Kolesníková

Беллоче

Koucký

et al. 2022

A&A

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“…Hernández and co‐workers [109] showed that TiO 2 , a prebiotically plausible mineral, combined with mechanochemical activation, promoted oligomerization of glycine at ambient temperature and in the absence of water (Scheme 19). The milling temperature has proven critical for the oligomerization process as raising the reaction temperature increases both the degree of oligomerization and the concomitant formation of undesired cyclic glycine dimer (DKP, Scheme 19 and Table 6).…”

Section: Mechanochemistry Vs Solvent‐based Chemistrymentioning

confidence: 99%

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

et al. 2022

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Mechanochemical transformations have made chemists enter unknown territories, forcing a different chemistry perspective. While questioning or revisiting familiar concepts belonging to solution chemistry, mechanochemistry has broken new ground, especially in the panorama of organic synthesis. Not only does it foster new "thinking outside the box", but it also has opened new reaction paths, allowing to overcome the weaknesses of traditional chemistry exactly where the use of well-established solution-based methodologies rules out progress. In this Review, the reader is introduced to an intriguing research subject not yet fully explored and waiting for improved understanding. Indeed, the study is mainly focused on organic transformations that, although impossible in solution, become possible under mechanochemical processing conditions, simultaneously entailing innovation and expanding the chemical space.This publication is part of a joint Special Collection of Chemistry-Methods and ChemSusChem including invited contributions focusing on "Methods and Applications in Mechanochemistry". Please visit chemsuschem.org/ collections to view all contributions.

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“…While many reactions of interest to the prebiotic chemistry field are in the solution phase (homogenous or heterogenous), solid-state chemical reactions could also be relevant to this field. It has been demonstrated that amino acids, nucleotides, nucleosides, peptides, and sugars can be formed under mechanochemical conditions [452][453][454][455]. Metal-mediated and metal-catalyzed reactions have been demonstrated under mechanochemical conditions [456].…”

Section: Solid-state Reactionsmentioning

confidence: 99%

Chirality in Organic and Mineral Systems: A Review of Reactivity and Alteration Processes Relevant to Prebiotic Chemistry and Life Detection Missions

et al. 2022

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Chirality is a central feature in the evolution of biological systems, but the reason for biology’s strong preference for specific chiralities of amino acids, sugars, and other molecules remains a controversial and unanswered question in origins of life research. Biological polymers tend toward homochiral systems, which favor the incorporation of a single enantiomer (molecules with a specific chiral configuration) over the other. There have been numerous investigations into the processes that preferentially enrich one enantiomer to understand the evolution of an early, racemic, prebiotic organic world. Chirality can also be a property of minerals; their interaction with chiral organics is important for assessing how post-depositional alteration processes could affect the stereochemical configuration of simple and complex organic molecules. In this paper, we review the properties of organic compounds and minerals as well as the physical, chemical, and geological processes that affect organic and mineral chirality during the preservation and detection of organic compounds. We provide perspectives and discussions on the reactions and analytical techniques that can be performed in the laboratory, and comment on the state of knowledge of flight-capable technologies in current and future planetary missions, with a focus on organics analysis and life detection.

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Mechanochemical Prebiotic Peptide Bond Formation**

Cited by 39 publications

References 84 publications

Laboratory rotational spectroscopy of acrylamide and a search for acrylamide and propionamide toward Sgr B2(N) with ALMA

Laboratory rotational spectroscopy of acrylamide and a search for acrylamide and propionamide toward Sgr B2(N) with ALMA

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

Chirality in Organic and Mineral Systems: A Review of Reactivity and Alteration Processes Relevant to Prebiotic Chemistry and Life Detection Missions

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