Video Experimental Relacionado

Updated: Dec 26, 2025

Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase

Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase

Published on: November 8, 2019

SeO₂-Transposición oxidativa mediada de los productos de Pauson-Khand

Sara E Dibrell¹, Michael R Maser¹, Sarah E Reisman¹

¹The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Journal of the American Chemical Society

|March 20, 2020

Resumen

El dióxido de selenio (SeO2) media las transposiciones oxidativas de las ciclopentenonas bicíclicas. Este método proporciona un acceso rápido a las ciclopentenonas funcionalizadas y oxidadas de los productos de la reacción de Pauson-Khand.

Área de la Ciencia:

Química orgánica
Metodología sintética
Reacciones de oxidación

Sus antecedentes:

Las ciclopentenonas bicíclicas son valiosos intermediarios sintéticos.
La reacción de Pauson-Khand (PKR) proporciona acceso a los andamios de la ciclopentenona.
La funcionalización oxidativa de estos sistemas sigue siendo un desafío sintético.

Objetivo del estudio:

Para revelar nuevas reacciones de transposición oxidativa de las ciclopentenonas cíclicas.
Desarrollar un método para la síntesis de ciclopentenonas di- y trioxidadas.
Para demostrar la utilidad sintética de los productos oxidados resultantes.

Principales métodos:

Tratamiento de los productos de la reacción de Pauson-Khand con dióxido de selenio (SeO2).
Variar la concentración de agua para controlar el grado de oxidación.
Estudios mecanicistas para elucidar las vías de oxidación concurrentes.
Funcionalización de productos oxidados mediante reacciones de acoplamiento cruzado.

Principales resultados:

El dióxido de selenio (SeO2) media eficientemente las transposiciones oxidativas de las ciclopentenonas bicíclicas.
Las ciclopentenonas di- y trioxidadas se obtienen en presencia y ausencia de agua, respectivamente.
Las vías de oxidación dependen del sustrato y de la concentración de agua.
Los productos oxidados son susceptibles de una mayor funcionalidad a través del acoplamiento cruzado.

Conclusiones:

Se establece una nueva vía sintética para las ciclopentenonas transpuestas oxidativamente.
El método permite un acceso rápido a estructuras complejas de ciclopentenona oxidadas.
Este trabajo amplía la utilidad sintética de los productos de la reacción de Pauson-Khand.

Más Videos Relacionados

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry

Published on: March 18, 2012

Anaerobic Protein Purification and Kinetic Analysis via Oxygen Electrode for Studying DesB Dioxygenase Activity and Inhibition

Anaerobic Protein Purification and Kinetic Analysis via Oxygen Electrode for Studying DesB Dioxygenase Activity and Inhibition

Published on: October 3, 2018

Videos de Conceptos Relacionados

Oxidation of Phenols to Quinones

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...

Pyruvate Oxidation

Pyruvate Oxidation

After glycolysis, the charged pyruvate molecules enter the mitochondria via active transport and undergo three enzymatic reactions. These reactions ensure that pyruvate can enter the next metabolic pathway so that energy stored in the pyruvate molecules can be harnessed by the cells.
First, the enzyme pyruvate dehydrogenase removes the carboxyl group from pyruvate and releases it as carbon dioxide. The stripped molecule is then oxidized and releases electrons, which are then picked up by NAD+...

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Phase I Oxidative Reactions: Overview

Phase I Oxidative Reactions: Overview

Phase I biotransformation, or functionalization, is a crucial chemical process that converts drugs and other xenobiotics into more water-soluble forms, facilitating expulsion from the body. It involves oxidative, reductive, and hydrolytic reactions that add or unveil polar functional groups on lipophilic substrates. Key players in phase I reactions are the mixed-function oxidases. Situated in liver cell microsomes, these enzymes predominantly carry out drug metabolism. They require molecular...

Oxidation and Reduction of Organic Molecules

Oxidation and Reduction of Organic Molecules

Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...

Radical Autoxidation

Radical Autoxidation

The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...