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Peroxisomes

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Peroxisomes are specialized organelles present in fungi, plant, and animal cells. It can vary in number, size, morphology, and activity depending on the type of tissue and the nutritional state of the cell. For example, cells with active lipid metabolism, such as adipocytes, neurons, and hepatocytes, have more peroxisomes than other cells in the body. Besides their primary role in breaking down complex organic molecules, peroxisomes can also synthesize specific macromolecules and participate in...
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Peroxisomes and mitochondria are two important oxygen-utilizing organelles in eukaryotic cells. Mitochondria carry out cellular respiration—the process that converts energy from food into ATP. Peroxisomes carry out a variety of functions, primarily breaking down different substances, such as fatty acids.
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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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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.
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Enolate Mechanism Conventions01:15

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When a carbonyl compound is treated with a strong base, the α position gets deprotonated to give a resonance-stabilized intermediate called an enolate. Enolates are ambident nucleophiles because they possess two nucleophilic sites that can attack an electrophile owing to the delocalization of the negative charge between the α carbon and oxygen atoms. When the oxygen atom attacks an electrophile, it is called O-attack, whereas electrophilic attack via the α carbon is known as...
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Protein Import into the Peroxisomes01:27

Protein Import into the Peroxisomes

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Cells contain membrane-bound organelles called peroxisomes that oxidize organic molecules by transferring hydrogen atoms to oxygen, producing hydrogen peroxide. Peroxisomes enzymatically convert the released hydrogen peroxide into water and oxygen.
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Structural basis for endoperoxide-forming oxygenases.

Takahiro Mori1,2,3, Ikuro Abe1,2

  • 1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Beilstein Journal of Organic Chemistry
|July 13, 2022
PubMed
Summary

This review explores endoperoxide natural products and their synthesis. It details the mechanisms of key enzymes like cyclooxygenase, FtmOx1, and NvfI in forming these vital compounds.

Keywords:
X-ray crystallographybiosynthesisendoperoxideenzymenatural products

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Area of Science:

  • Natural Product Chemistry
  • Organic Synthesis
  • Enzymology

Background:

  • Endoperoxide natural products are abundant and biologically active.
  • Their unique chemical structures drive interest in natural product research and synthesis.
  • Understanding their formation is crucial for medicinal chemistry and drug discovery.

Purpose of the Study:

  • To review structural analyses of endoperoxide-forming oxygenases.
  • To investigate the reaction mechanisms of these enzymes.
  • To summarize proposed pathways for endoperoxide biosynthesis.

Main Methods:

  • Literature review of structural data.
  • Analysis of mechanistic studies on oxygenases.
  • Compilation of proposed reaction mechanisms.

Main Results:

  • Detailed examination of cyclooxygenase mechanisms.
  • In-depth analysis of fumitremorgin B endoperoxidase (FtmOx1).
  • Exploration of asnovolin A endoperoxygenase (NvfI) pathways.

Conclusions:

  • Endoperoxide-forming oxygenases are key to producing diverse natural products.
  • Mechanistic insights facilitate synthetic strategies and drug development.
  • Further research can unlock new therapeutic applications of endoperoxides.