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Oxidation of Alcohols02:37

Oxidation of Alcohols

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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Radical Oxidation of Allylic and Benzylic Alcohols01:21

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Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Protection of Alcohols02:31

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This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin
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HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

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Vanillyl alcohol oxidase.

Tom A Ewing1, Gudrun Gygli2, Marco W Fraaije3

  • 1Wageningen Food & Biobased Research, Wageningen University & Research, Wageningen, The Netherlands.

The Enzymes
|September 21, 2020
PubMed
Summary
This summary is machine-generated.

Vanillyl alcohol oxidase (VAO) from Penicillium simplicissimum is a key flavoprotein. Research covers its discovery, function, structure, and engineering for substrate specificity.

Keywords:
Catalytic mechanismCovalent flavinylationCrystal structureEnantioselectivityEnzyme dynamicsFlavoprotein familyLignin and phenolsOxidasePhylogeneticsSuicide inhibition

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Area of Science:

  • Biochemistry
  • Enzymology
  • Protein Science

Background:

  • Vanillyl alcohol oxidase (VAO) is a flavoprotein from Penicillium simplicissimum, belonging to the VAO/PCMH family.
  • This review details the historical research and key characteristics of VAO.

Purpose of the Study:

  • To provide a comprehensive historical overview of vanillyl alcohol oxidase (VAO) research.
  • To elucidate the enzyme's physiological role, catalytic mechanism, structure, and substrate specificity.

Main Methods:

  • Literature review of VAO research.
  • Analysis of biochemical characterization, structural studies, and protein engineering data.
  • Summary of computational and phylogenetic analyses.

Main Results:

  • VAO's discovery, biochemical properties, and physiological role are detailed.
  • The enzyme's three-dimensional structure, catalytic mechanism, and covalent flavinylation are reviewed.
  • Protein engineering studies revealed insights into substrate specificity and enantioselectivity.

Conclusions:

  • VAO is a well-characterized flavoprotein with significant implications in enzymology.
  • Further research, including computational studies, continues to refine our understanding of VAO.
  • The phylogenetic distribution highlights the importance of VAO and related enzymes.