Absolute asymmetrische Synthese: Ursprung, Beeinflussung und Verstärkung von Chiralität

Feringa, Ben L.; Delden, Richard A. van

doi:10.1002/(sici)1521-3757(19991203)111:23<3624::aid-ange3624>3.0.co;2-x

Cited by 180 publications

(15 citation statements)

References 215 publications

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“…This is attributed either to unknown chiral impurities in the solvent192 or to tiny stochastic ee ’s 193. This finding is of great significance as it supports arguments that biological homochirality is a statistical inevitability20, 162 rather than a biological “invention” or the product of deterministic physical forces.…”

Section: Asymmetric Autocatalysissupporting

confidence: 58%

“…Asymmetric autocatalysis is of special interest as it may be related to the origin of biomolecular homochirality 20. 21, 162 This topic has fascinated scientists since Pasteur, is of significant contemporary interest, and has been extensively reviewed from several perspectives (for example, see Ref.…”

Section: Asymmetric Autocatalysismentioning

confidence: 99%

“…If each enantiomer is autocatalytically active, but heterochiral dimers of the autocatalyst are inactive, then very small ee values can be amplified to high ee . Small ee ’s may arise stochastically or from a variety of physical sources 20. The Frank model has been experimentally realized by Soai and co‐workers (Section 5.1).…”

Section: Introductionmentioning

confidence: 99%

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Mechanisms of Autocatalysis

Bissette¹,

Fletcher²

2013

Angew Chem Int Ed

347

268

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Self-replication is a fundamental concept. The idea of an entity that can repeatedly create more of itself has captured the imagination of many thinkers from von Neumann to Vonnegut. Beyond the sciences and science fiction, autocatalysis has found currency in economics and language theory, and has raised ethical fears memorably summed up by the "gray goo" trope. Autocatalysis is central to the propagation of life and intrinsic to many other biological processes. This includes the modern conception of evolution, which has radically altered humanity's image of itself. Organisms can be thought of as imperfect self-replicators which produce closely-related species, allowing for selection and evolution. Hence, any consideration of self-replication raises one of the most profound questions of all: what is life? Minimal self-replicating systems have been studied with the aim of understanding the principles underlying living systems, allowing us to refine our concepts of biological fitness and chemical stability, self-organization and emergence, and ultimately to discover how chemistry may become biology.

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Section: Asymmetric Autocatalysissupporting

confidence: 58%

Section: Asymmetric Autocatalysismentioning

confidence: 99%

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Mechanisms of Autocatalysis

Bissette¹,

Fletcher²

2013

Angew Chem Int Ed

347

268

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“…Several theories have been proposed as to the origin of homochirality in organic compounds,1–5 for example, theories involving circularly polarized light,9, 10 chiral inorganic crystals such as quartz,11 or absolute asymmetric synthesis 2. 4, 12, 13 Small enantiomeric imbalances induced by these mechanisms have been amplified significantly by asymmetric autocatalysis to afford highly enantioenriched compounds 12–23…”

Section: Methodsmentioning

confidence: 99%

Achiral Nucleobase Cytosine Acts as an Origin of Homochirality of Biomolecules in Conjunction with Asymmetric Autocatalysis

et al. 2007

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Crystals to add chirality: Cytosine, a prebiotic achiral biomolecule and an essential nucleobase, spontaneously forms enantioenriched crystals if stirring is applied during crystallization. The chiral crystal of achiral cytosine is a chiral initiator for asymmetric autocatalysis of a pyrimidyl alkanol with amplification of the ee value, which provides a nearly enantiopure alcohol with an absolute configuration correlated to that of the cytosine crystal.

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“…Ever since the famous experiment of Pasteur,1 scientists have tried to generate excess left‐ or right‐handed chiral molecules from achiral precursors without the intervention of preexisting molecular chirality. This problem, called absolute asymmetric synthesis, has turned out to be a major challenge 2…”

Section: Calculated Vibrational Modes Of Clnb Molecule In the Gas Phamentioning

confidence: 99%

Chirality Change of Chloronitrobenzene on Au(111) Induced by Inelastic Electron Tunneling

2009

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Chirality chameleon: Inelastic electron tunneling manipulation can be used to change a single chloronitrobenzene (ClNB) molecule, randomly adsorbed on Au(111), into its desired enantiomeric form (r or l, see STM images and ball-and-stick representation) and to vary its rotational orientation. The different threshold voltages for chirality change (260 mV) and rotation (380 mV) allow these processes to be induced separately.

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Absolute asymmetrische Synthese: Ursprung, Beeinflussung und Verstärkung von Chiralität

Cited by 180 publications

References 215 publications

Mechanisms of Autocatalysis

Mechanisms of Autocatalysis

Achiral Nucleobase Cytosine Acts as an Origin of Homochirality of Biomolecules in Conjunction with Asymmetric Autocatalysis

Chirality Change of Chloronitrobenzene on Au(111) Induced by Inelastic Electron Tunneling

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