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A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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Relating Reaction Mechanisms
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
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Formación de nitrito en un complejo de diiron dinitrosyl

Anna L Poptic1, Jeffrey K Klinger1, Samantha L Carter1

  • 1Department of Chemistry & Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio43210, United States.

Journal of the American Chemical Society
|October 10, 2023
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio presenta un nuevo complejo de diironio sintético que imita la actividad oxidante del óxido nítrico (NO) de una enzima bacteriana. El complejo modelo convierte con éxito el NO en nitrito, ofreciendo información sobre los mecanismos de evasión inmune bacteriana.

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Área de la Ciencia:

  • Química bioorgánica
  • Imitación de enzimas
  • Patogénesis bacteriana

Sus antecedentes:

  • Las bacterias patógenas utilizan enzimas que contienen hierro para desintoxicar el óxido nítrico (NO), una molécula inmune de mamíferos.
  • Las reductasas de óxido nítrico de flavodiero (FNOR) y las proteínas similares a la hemeritrina (HLP) son enzimas bacterianas clave involucradas en el metabolismo del NO.
  • Mientras que los FNOR reducen el NO, ciertos HLP como el Mka-HLP oxidan el NO a nitrito, una función que aún no se ha reproducido en modelos sintéticos.

Objetivo del estudio:

  • Para sintetizar un nuevo complejo de diirón que modela el sitio activo pobre en electrones de Mka-HLP.
  • Investigar la reactividad de oxido nítrico (NO) de este complejo sintético.
  • Proporcionar el primer modelo sintético que replique la actividad de la NO oxidasa observada en Mka-HLP.

Principales métodos:

  • Síntesis de un nuevo complejo de diirón diseñado para imitar el entorno de coordinación pobre en electrones de Mka-HLP.
  • Reacción del precursor diferroso con el óxido nítrico (NO) para formar las especies diiron dinitrosil y mononitrosil.
  • Aislamiento, caracterización y ensayo funcional de las especies de nitrosilo resultantes, centradas en la oxidación de NO.

Principales resultados:

  • Se formó y caracterizó una especie diiron dinitrosyl ({FeNO}2) y una especie mononitrosyl diiron (Fe{FeNO}).
  • La oxidación de la especie diiron dinitrosyl ({FeNO}2) produjo nitrito con una alta eficiencia del 71%.
  • Esto demuestra la primera replicación sintética exitosa de la actividad de la NO oxidasa de Mka-HLP.

Conclusiones:

  • El complejo de diirón sintetizado modela efectivamente la función de la NO oxidasa de Mka-HLP.
  • El estudio sugiere la participación de especies {FeNO}2/{FeNO} como intermediarios en este proceso de oxidación del NO.
  • Este trabajo proporciona información valiosa sobre las estrategias bacterianas para la desintoxicación de NO y la evasión inmune.