Molecular Chirality in Meteorites and Interstellar Ices, and the Chirality Experiment on Board the ESA Cometary Rosetta Mission

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

doi:10.1002/anie.201409354

Cited by 62 publications

(43 citation statements)

References 156 publications

(226 reference statements)

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“…1 The single handedness in living systems furthermore implies that the two enantiomers of a molecule interact differently with chiral biomolecular receptors. Although any object has a mirror image, not every mirror image is identical to the original.…”

Section: (1) Introductionmentioning

confidence: 99%

Viedma ripening: a reliable crystallisation method to reach single chirality

Sögütoglu¹,

Steendam²,

Meekes³

et al. 2015

Chem. Soc. Rev.

182

170

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Crystallisation processes have evolved to practical methods that allow isolation of an enantiopure product in high yield. Viedma ripening in particular enables access to enantiopure products in a reliable way, simply through grinding of crystals in a solution. This tutorial review covers the basic principles behind asymmetric crystallisation processes, with an emphasis on Viedma ripening, and shows that to date many novel organic molecules can be obtained in enantiopure solid form.

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Section: (1) Introductionmentioning

confidence: 99%

Viedma ripening: a reliable crystallisation method to reach single chirality

Sögütoglu¹,

Steendam²,

Meekes³

et al. 2015

Chem. Soc. Rev.

182

170

View full text Add to dashboard Cite

show abstract

“…Glutamic acid was reported to be synthesized in experiments such as the hydrogen sulfide‐rich spark discharge experiment . Though proline was not reported being synthesized in this experiment, it has been found extensively on meteorites . What is perhaps more interesting, however, is the properties of this reaction scheme on primordial Earth.…”

Section: Resultsmentioning

confidence: 85%

Proline autocatalysis in the origin of biological enantioenriched chirality

Sadagopan

2018

Chirality

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Biological enantioenriched chirality is a phenomenon that in living organisms, amino acids and carbohydrates typically have the same absolute configuration. Perhaps one of the earliest attempts to delineate the origins of this phenomenon was a theory known as asymmetric autocatalysis, a reaction in which the structures of the chiral catalyst and the product are the same, and in which the chiral product acts as a chiral catalyst for its own production. In theory, this would mean that small asymmetries in the product will propagate rapidly. However, autocatalysis also relies on the cross‐inhibition of chiral states, something that would not likely be possible on primordial Earth. But recently, theories on asymmetric autocatalysis have begun to resurface as more recent findings indicate that other mechanisms exist to stabilize the homochiral states. In this study, I propose an autocatalytic cycle, and using density functional theory, prove that (1) it is plausible on primordial Earth, and (2) it propagates arbitrary asymmetries in proline. Thus, facilitating asymmetry in proline and allowing access to a wide variety of asymmetric proline‐catalyzed reactions, including those involved in the synthesis of amino acids and carbohydrates from achiral precursors.

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“…Although this is a very exciting concept, there are only a limited number of absolute asymmetric syntheses known today . To induce symmetry‐breaking, several means have been used, such as irradiation with circularly polarized light, or application of rotational and magnetic forces, or attrition‐enhanced deracemization . The most popular approach so far involves the use of chiral crystals of achiral or racemic compounds .…”

Section: Introductionmentioning

confidence: 99%

Frozen Chirality of Tertiary Aromatic Amides: Access to Enantioenriched Tertiary α‐Amino Acid or Amino Alcohol without Chiral Reagent

Thoa

Viswambharan

Gori

et al. 2017

Chemistry A European J

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One of the fundamental and intriguing aspects of life is the homochirality of the essential molecules. In this field, the absolute asymmetric synthesis of α-amino acids is a major challenge. Herein, we report access, by chemical means, to tertiary α-amino acid derivatives in up to 96 % ee without using any chiral reagent. In our strategy, the dynamic axial chirality of tertiary aromatic amides is frozen in a crystal and is responsible for the stereoselectivity of the subsequent steps. Furthermore, we could control the configuration of the final product by manually sorting and selecting the initial crystals. Based on vibrational circular dichroism studies, we could rationalize the observed stereoselectivity.

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Molecular Chirality in Meteorites and Interstellar Ices, and the Chirality Experiment on Board the ESA Cometary Rosetta Mission

Cited by 62 publications

References 156 publications

Viedma ripening: a reliable crystallisation method to reach single chirality

Viedma ripening: a reliable crystallisation method to reach single chirality

Proline autocatalysis in the origin of biological enantioenriched chirality

Frozen Chirality of Tertiary Aromatic Amides: Access to Enantioenriched Tertiary α‐Amino Acid or Amino Alcohol without Chiral Reagent

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