Video Experimental Relacionado

Updated: Mar 22, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

El catabolismo del dibenzotiofeno se produce a través de un intermediario de N5-óxido de flavina

Sanjoy Adak¹, Tadhg P Begley¹

¹Department of Chemistry, Texas A&M University , 3255 TAMU, College Station, Texas 77843, United States.

Journal of the American Chemical Society

|April 28, 2016

Resumen

La flavoenzima DszA cataliza un paso clave en la degradación del dibenzotiofeno. Los estudios mecanicistas revelan un intermediario de flavin-N5-óxido, crucial para la conversión del dibenzotiofeno sulfona en ácido 2- ((2-hidroxifenilo) -benzenosulfínico.

Área de la Ciencia:

La bioquímica
Enzimología
Metabolismo microbiano

Sus antecedentes:

El dibenzotiofeno (DBT) es un contaminante organosulfuroso persistente que se encuentra en los combustibles fósiles.
La degradación microbiana del DBT es esencial para la remediación ambiental.
La enzima DszA cataliza el tercer paso en la vía catabólica del DBT, convirtiendo el sulfón del DBT.

Objetivo del estudio:

Para aclarar el mecanismo de reacción de la flavoenzima DszA.
Identificar los intermediarios clave en la conversión del dibenzotiofeno sulfona.
Para confirmar el papel del óxido de flavina-N5 en la reacción catalizada por DszA.

Principales métodos:

Estudios mecánicos que incluyen análisis cinéticos y espectroscópicos.
Espectrometría de masas por cromatografía líquida (LC-MS) para la detección intermedia.
Experimentos de coelución y (18) estudios de etiquetado de O2 para confirmar la identidad del intermediario.

Principales resultados:

El mecanismo de reacción implica el hidroperoxido C2 del dibenzotiofeno sulfona.
Se propuso y detectó un intermediario de flavin-N5-óxido.
El análisis LC-MS y el etiquetado con (18) O2 confirmaron la intermediación entre la flavina y el óxido N5.

Conclusiones:

DszA utiliza un intermediario de flavin-N5-óxido para la conversión de dibenzotiofeno sulfona.
Este hallazgo proporciona información crucial sobre el mecanismo enzimático de la degradación de los compuestos organosulfurados.
El estudio mejora nuestra comprensión de las vías microbianas para la biorremediación de contaminantes.

Más Videos Relacionados

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Videos de Conceptos Relacionados

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems

Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems

Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...

Role of Reduced Coenzymes NADH and FADH₂

Role of Reduced Coenzymes NADH and FADH₂

The energy released from the breakdown of the chemical bonds within nutrients can be stored either through the reduction of electron carriers or in the bonds of adenosine triphosphate (ATP). In living systems, a small class of compounds functions as mobile electron carriers, molecules that bind to and shuttle high-energy electrons between compounds in pathways. The principal electron carriers that will be considered originate from the B vitamin group and are derivatives of nucleotides; they are...

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...