Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Esters to β-Ketoesters: Claisen Condensation Mechanism

Esters to β-Ketoesters: Claisen Condensation Mechanism

Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

β-Dicarbonyl Compounds via Crossed Claisen Condensations

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Unusual Acyltransferase Negatively Regulates Nigericin Production via Malonylation of P450 NigD<sub>Sy</sub>.

Journal of agricultural and food chemistry·2026

Same author

Engineering Substrate Promiscuity and Catalytic Efficiency of Benzylisoquinoline Alkaloids <i>N</i>-Methyltransferases.

Journal of agricultural and food chemistry·2026

Same author

Genome-Driven Discovery of Anti-MDR Bacterial Heptapeptides from a Cold-Seep-Derived <i>Bacillus</i> Strain.

Molecules (Basel, Switzerland)·2026

Same author

Discovery of Antimicrobial Oligoindoles from a Cold-Seep-Derived <i>Halomonas</i> Strain.

Marine drugs·2026

Same author

Discovery and Characterization of a Single-Component Halogenase for Phenazine Halogenation.

Organic letters·2025

Same author

Characterization of the Biosynthesis of Pimprinine-Type Indolyloxazoles Unravels an Unusual d-Configurational Substrate Metabolic Streamline.

Journal of the American Chemical Society·2025

Search research articles

Related Experiment Video

Updated: Jul 1, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

A Versatile Thioesterase Involved in Dimerization during Cinnamoyl Lipid Biosynthesis.

Zirong Deng^1,2, Chunni Liu¹, Fang Wang²

¹State Key Laboratory for Crop Stress Resistance and High-Efficiency Production, Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shannxi, 712100, China.

Angewandte Chemie (International Ed. in English)

|March 10, 2024

Summary

Researchers identified a unique thioesterase (TE) gene, ysfF, responsible for the dearomatization/dimerization process in youssoufene A1. This discovery sheds light on the biosynthesis of this potent antimicrobial compound.

Keywords:

biosynthesis cinnamoyl lipids dimerization thioesterase

More Related Videos

Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers

Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers

Published on: November 22, 2015

Metabolic Pathway Confirmation and Discovery Through 13C-labeling of Proteinogenic Amino Acids

Metabolic Pathway Confirmation and Discovery Through 13C-labeling of Proteinogenic Amino Acids

Published on: January 26, 2012

Related Experiment Videos

Last Updated: Jul 1, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers

Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers

Published on: November 22, 2015

Metabolic Pathway Confirmation and Discovery Through 13C-labeling of Proteinogenic Amino Acids

Metabolic Pathway Confirmation and Discovery Through 13C-labeling of Proteinogenic Amino Acids

Published on: January 26, 2012

Area of Science:

Biochemistry
Molecular Biology
Natural Product Biosynthesis

Background:

Youssoufene A1, a dimeric cinnamoyl lipid, shows potent inhibition against multidrug-resistant Enterococcus faecalis.
The biosynthesis pathway for youssoufene A1, particularly its dearomatization/dimerization, remains unelucidated.

Purpose of the Study:

To functionally characterize the thioesterase (TE) gene ysfF involved in youssoufene A1 biosynthesis.
To elucidate the mechanism of dearomatization and dimerization in youssoufene A1 formation.

Main Methods:

Functional characterization of the "gene-within-gene" thioesterase (TE) gene ysfF.
Intracellular tagged carrier-protein tracking (ITCT) strategy.
In vitro reconstitution and in vivo experiments.
Site-directed mutagenesis.

Main Results:

The ysfF gene encodes two proteins: full-length YsfF and nested YsfF_HBT, both possessing thioesterase activities.
YsfF/YsfF_HBT facilitate 6π-electrocyclic ring closure for benzene ring formation.
YsfF and cyclase YsfX collaborate in ACP-tethered dearomatization/dimerization via a potential Michael-type addition.
Specific residues (N301, E483, H566) in YsfF are crucial for these reactions.

Conclusions:

This study reveals the dual role of YsfF in thioesterase activity and facilitating dearomatization/dimerization.
The findings uncover an unprecedented biosynthetic mechanism involving YsfF and YsfX.
Enhances understanding of thioesterase (TE) protein family multifunctionality and natural product biosynthesis.