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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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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.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
3.9K
Oxidation of Alcohols02:37

Oxidation of Alcohols

13.0K
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:
13.0K
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

3.6K
Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
3.6K
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

6.2K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.2K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.1K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.1K

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Related Experiment Video

Updated: Jun 28, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

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Efficient synthesis 1,4-cyclohexanedicarboxaldehyde by an engineered alcohol oxidase.

Yaqi Cheng1, Wei Song1, Xiulai Chen2

  • 1School of Life Sciences and Health Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, 214122, China.

Bioresources and Bioprocessing
|April 22, 2024
PubMed
Summary

Researchers engineered an alcohol oxidase (AOX) enzyme to efficiently produce 1,4-cyclohexanedicarboxaldehyde (CHDA) from 1,4-cyclohexanedimethanol (CHDM). This enhanced enzyme variant shows significant potential for industrial CHDA production.

Keywords:
1,4-CyclohexanedicarboxaldehydeAlcohol oxidasePrimary alcohol oxidation reactionProtein engineering

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Area of Science:

  • Biocatalysis
  • Enzyme Engineering
  • Organic Synthesis

Background:

  • Flavin adenine dinucleotide (FAD)-dependent alcohol oxidases (AOX) catalyze primary alcohol oxidation.
  • High energy barriers in hydride transfer limit the catalytic efficiency of wild-type AOX.
  • 1,4-cyclohexanedicarboxaldehyde (CHDA) is a key intermediate for spiral compounds.

Purpose of the Study:

  • To engineer an AOX for enhanced production of CHDA from 1,4-cyclohexanedimethanol (CHDM).
  • To elucidate the mechanism of AcCO-catalyzed primary alcohol oxidation and identify rate-limiting steps.
  • To improve catalytic efficiency by reducing the energy barrier for hydride transfer.

Main Methods:

  • Analysis of Arthrobacter cholorphenolicus alcohol oxidase (AcCO) structure and catalytic mechanism.
  • Protein engineering strategy to adjust active conformation and shorten hydride transfer distance.
  • Whole-cell biocatalysis using engineered Escherichia coli for CHDA production.

Main Results:

  • Identified hydride transfer energy barriers (13.4 and 20.4 kcal·mol⁻¹) limiting wild-type AcCO efficiency.
  • Developed variant W4 (S101A/H351V/N378S/Q329N) with 112.5-fold increased catalytic efficiency for CHDA production.
  • Achieved 29.6 g·L⁻¹ titer and 42.2% yield of CHDA in a 3 L scale preparation using E. coli whole-cell catalyst.

Conclusions:

  • Protein engineering successfully reduced the energy barrier for hydride transfer in AOX.
  • Engineered AOX variant W4 demonstrates significantly enhanced CHDA production capabilities.
  • The developed biocatalytic system holds promise for industrial-scale CHDA synthesis.