Related Experiment Video
Updated: Jan 5, 2026
09:58
Light-driven Enzymatic Decarboxylation
Published on: May 22, 2016
12.1K
Tailoring chemoenzymatic oxidation via in situ peracids
Rebecca N Re1, Johanna C Proessdorf, James J La Clair
1Department of Chemistry and Biochemistry, UC San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA. mburkart@ucsd.edu.
Organic & Biomolecular Chemistry
|October 26, 2019
Summary
This study introduces a two-phase enzymatic system for safe in situ peracid generation, enabling efficient olefin and lipid epoxidation. This green chemistry approach simplifies handling and offers scalable synthetic applications.
Area of Science:
- Green chemistry
- Biocatalysis
- Organic synthesis
Background:
- Peracids are essential for epoxidation but challenging to handle, necessitating in situ generation.
- Current methods for peracid generation can be hazardous or inefficient.
Purpose of the Study:
- To develop a safe and efficient two-phase enzymatic system for in situ peracid generation.
- To apply this system for the epoxidation of olefins and lipids, and for sulfide oxidation.
Main Methods:
- Utilized a two-phase system with enzymes for peracid generation.
- Applied the generated peracids for epoxidation of various substrates.
- Demonstrated utility in lipid and olefin epoxidation and sulfide oxidation.
Main Results:
- Successfully generated peracids in situ using an enzymatic system.
- Achieved effective epoxidation of olefins and lipids.
- Showcased applicability to sulfide oxidation.
Conclusions:
- The developed enzymatic system offers a safer and greener alternative for peracid-mediated oxidations.
- This method provides a scalable approach for synthetic modifications and sustainable chemical processes.
Related Concept Videos
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
7.1K
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.
7.1K
01:20Radical Autoxidation
3.0K
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...
3.0K
02:01Alkynes to Carboxylic Acids: Oxidative Cleavage
6.6K
Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
6.6K
01:46Oxidative Cleavage of Alkenes: Ozonolysis
12.6K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
12.6K
01:07Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
4.3K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
4.3K
01:31Preparation of Carboxylic Acids: Overview
3.5K
There are various methods for the preparation of carboxylic acids. For example, oxidation of primary alcohols or aldehydes using strong oxidizing agents results in a carboxylic acid. Aldehydes can also be oxidized in the presence of mild oxidizing agents.
3.5K