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Videos de Conceptos Relacionados

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Radical Formation: Elimination00:51

Radical Formation: Elimination

1.9K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
1.9K
Radical Formation: Addition00:47

Radical Formation: Addition

1.8K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.8K
Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

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In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
1.5K
Radical Formation: Overview01:03

Radical Formation: Overview

2.2K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
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Evolución dirigida de las enzimas de hierro no hemo para acceder a la azidación C ((sp3)

Jinyan Rui1, Qun Zhao1, Anthony J Huls1

  • 1Department of Chemistry, Johns Hopkins University, Baltimore, MD 21218, USA.

Science (New York, N.Y.)
|May 19, 2022
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores reprogramaron las enzimas de hierro no hemo para la azidación abiológica C ((sp3) -H utilizando un relé de radicales catalizados por hierro. Este biocatálisis logra un alto exceso enantiomérico y números de rotación, abriendo nuevas vías para el desarrollo de catalizadores de metalloenzimas.

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Área de la Ciencia:

  • Biocatálisis y ingeniería enzimática
  • Síntesis orgánica y catálisis
  • Química de las metaloproteínas

Sus antecedentes:

  • Las enzimas de hierro no hemo son catalizadores versátiles que se encuentran en la naturaleza.
  • Las transformaciones abiológicas, como la azidación C ((sp3) -H, son sintéticamente valiosas pero desafiantes.
  • Los mecanismos de relevo radicales ofrecen estrategias poderosas para la síntesis orgánica compleja.

Objetivo del estudio:

  • Para reprogramar las enzimas de hierro no hemo para una nueva reacción de azidación abiológica C ((sp3) -H.
  • Para utilizar el relevo de radicales catalizados por hierro para una azidación biocatalítica eficiente.
  • Desarrollar una plataforma de detección de alto rendimiento para la evolución de las enzimas.

Principales métodos:

  • La reprogramación de las enzimas de hierro no hemo.
  • Mecanismo de relevo de radicales catalizados por hierro que incluye radicales amidil y intermedios Fe (III) -N3.
  • Plataforma de cribado de alto rendimiento que utiliza la química de clic para la evolución de las enzimas.

Principales resultados:

  • Catálisis exitosa de una reacción de azidación abiológica C ((sp3) -H.
  • Las variantes de enzimas optimizadas lograron hasta 10.600 pérdidas totales.
  • Se obtuvo un alto exceso enantiomérico (hasta el 93%) para los productos de azidación.

Conclusiones:

  • Demostró la viabilidad de la reprogramación de enzimas de hierro no hemo para las transformaciones abiológicas.
  • Destacó el potencial del relé de radicales catalizados por hierro en el biocatálisis.
  • Se prevén aplicaciones más amplias de metalloenzimas diseñadas para nuevas reacciones sintéticas.