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Related Concept Videos

Oxidation of Phenols to Quinones01:17

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 property is crucial in...
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems01:19

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...
Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems01:15

Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems

Oxidative reactions are pivotal in metabolizing numerous compounds, including pharmaceutical drugs. These reactions often occur in carbon-heteroatom systems, such as carbon-nitrogen, carbon-sulfur, and carbon-oxygen.
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
Phase I Oxidative Reactions: Overview01:19

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...
Radical Autoxidation01:20

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...
Oxidation and Reduction of Organic Molecules01:19

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...

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Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry
12:08

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

Published on: March 18, 2012

Singlet oxygen reactions with flavonoids. A theoretical-experimental study.

Javier Morales1, Germán Günther, Antonio L Zanocco

  • 1Universidad de Chile, Facultad de Ciencias Químicas y Farmacéuticas, Departamento de Ciencias y Tecnología Farmacéuticas, Santiago, Chile.

Plos One
|July 18, 2012
PubMed
Summary

Flavonoids effectively quench singlet oxygen, acting as potent antioxidants. Their reaction rate constants vary by structure, suggesting potential benefits in oxidative stress conditions, especially with a flavonoid-rich diet.

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Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
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Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase
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Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase

Published on: November 8, 2019

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Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry
12:08

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

Published on: March 18, 2012

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
09:50

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Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase
10:14

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

Published on: November 8, 2019

Area of Science:

  • Biochemistry
  • Photochemistry
  • Medicinal Chemistry

Background:

  • Singlet oxygen is a reactive oxygen species implicated in oxidative stress.
  • Flavonoids are plant-derived compounds with known antioxidant properties.
  • Understanding flavonoid-singlet oxygen interactions is crucial for their application as antioxidants.

Purpose of the Study:

  • To quantify the reaction rate constants between singlet oxygen and various flavonoids.
  • To investigate the structural basis for flavonoid reactivity with singlet oxygen.
  • To assess the potential of flavonoids as antioxidants in biological systems.

Main Methods:

  • Detection of singlet oxygen emission at 1270 nm.
  • Laser excitation and steady-state methods to determine total (k(T)) and reactive (k(r)) rate constants.
  • Electronic structure calculations (global descriptors, Fukui functions) to analyze molecular structure-reactivity relationships.

Main Results:

  • Total reaction rate constants (k(T)) ranged from 2.4×10(7) to 13.4×10(7) M(-1)s(-1).
  • Reactive rate constants (k(r)) ranged from 2.8×10(5) to 65.7×10(5) M(-1)s(-1).
  • Epicatechin and catechin showed minimal reactivity; others were good singlet oxygen quenchers.

Conclusions:

  • All studied flavonoids are effective singlet oxygen quenchers.
  • Flavonoid structure influences reactivity, with charge transfer exciplex formation observed.
  • These findings support the use of flavonoids as antioxidants, particularly in diets rich in these compounds.