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Related Concept Videos

Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Halogenation of Alkenes02:46

Halogenation of Alkenes

15.6K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
15.6K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.9K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
12.9K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.0K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.0K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.2K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.2K
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

4.1K
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
4.1K

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Updated: Jun 29, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

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β-Dicarbonyls Facilitate Engineered Microbial Bromoform Biosynthesis.

Thomas D Loan1, Claudia E Vickers2,3, Michael Ayliffe1

  • 1CSIRO Agriculture and Food, Box 1700, Clunies Ross Street, Canberra 2601, Australia.

ACS Synthetic Biology
|March 25, 2024
PubMed
Summary
This summary is machine-generated.

Scientists engineered yeast to produce bromoform, a compound that inhibits methane production in livestock. This offers a sustainable, scalable alternative to seaweed-based feed additives for reducing agricultural greenhouse gas emissions.

Keywords:
bromoformhalogenationhaloperoxidasemethanerumen

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Elucidating the Metabolism of 2,4-Dibromophenol in Plants
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Elucidating the Metabolism of 2,4-Dibromophenol in Plants

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Area of Science:

  • Biotechnology
  • Environmental Science
  • Microbiology

Background:

  • Ruminant livestock contribute significantly to global methane emissions (24%).
  • Bromoform, found in Asparagopsis seaweeds, effectively inhibits ruminal methanogenesis.
  • Current seaweed-based solutions face scalability challenges to meet global demand.

Purpose of the Study:

  • To engineer a novel microbial biosynthesis pathway for sustainable, large-scale bromoform production.
  • To develop yeast as an alternative biological source for bromoform synthesis.
  • To advance microbial halogenation pathways.

Main Methods:

  • Engineered Saccharomyces cerevisiae to express a vanadate-dependent haloperoxidase gene.
  • Identified and utilized β-dicarbonyl compounds with low pKa as essential substrates.
  • Demonstrated in vivo bromoform synthesis in engineered yeast.

Main Results:

  • Successfully synthesized bromoform in engineered yeast.
  • Established a proof-of-concept for microbial bromoform production.
  • Identified key substrates required for the biosynthesis pathway.

Conclusions:

  • Yeast can be engineered for sustainable, scalable bromoform production via fermentation.
  • This approach offers a promising alternative to seaweed-based methane mitigation strategies.
  • The study advances the field of microbial biosynthesis for halogenated compounds.