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Related Concept Videos

Esters to Carboxylic Acids: Saponification01:25

Esters to Carboxylic Acids: Saponification

Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

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 alkylated β-keto acid.
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

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 intermediate restores...

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Related Experiment Video

Updated: May 29, 2026

Evaluation of Substrate Ubiquitylation by E3 Ubiquitin-ligase in Mammalian Cell Lysates
09:47

Evaluation of Substrate Ubiquitylation by E3 Ubiquitin-ligase in Mammalian Cell Lysates

Published on: May 10, 2022

Ubiquitination of substrates by esterification.

Xiaoli Wang1, Roger A Herr, Ted H Hansen

  • 1Department of Pathology and Immunology, Washington University School of Medicine, St. Louis, MO 63110, USA. xiwang@wustl.edu

Traffic (Copenhagen, Denmark)
|September 3, 2011
PubMed
Summary

Ubiquitination, a key protein modification, can now be understood to occur via esterification on cysteine, serine, and threonine residues, expanding its known mechanisms and physiological roles.

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Last Updated: May 29, 2026

Evaluation of Substrate Ubiquitylation by E3 Ubiquitin-ligase in Mammalian Cell Lysates
09:47

Evaluation of Substrate Ubiquitylation by E3 Ubiquitin-ligase in Mammalian Cell Lysates

Published on: May 10, 2022

In Vitro Ubiquitination and Deubiquitination Assays of Nucleosomal Histones
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In Vitro Ubiquitination and Deubiquitination Assays of Nucleosomal Histones

Published on: July 25, 2019

In Vitro Analysis of E3 Ubiquitin Ligase Function
06:06

In Vitro Analysis of E3 Ubiquitin Ligase Function

Published on: May 14, 2021

Area of Science:

  • Biochemistry
  • Molecular Biology
  • Cell Biology

Background:

  • Post-translational modification by ubiquitination regulates protein localization and function.
  • Traditionally, ubiquitination was thought to occur exclusively via isopeptide or peptide bonds to lysine residues or the N-terminus.
  • The existence of ubiquitination-dependent protein fates in lysine-deficient proteins presented a paradox.

Purpose of the Study:

  • To review recent evidence for ubiquitination occurring through esterification.
  • To explore the mechanisms and physiological significance of esterification in ubiquitination.
  • To address the paradox of ubiquitination in lysine-deficient proteins.

Main Methods:

  • Literature review of recent studies on protein ubiquitination.
  • Analysis of biochemical evidence for thio- and oxy-ester bond formation in ubiquitination.
  • Discussion of experimental findings supporting esterification as a functional ubiquitination pathway.

Main Results:

  • Ubiquitination can occur on cysteine (thioester) and serine/threonine (oxyester) residues, termed esterification.
  • These esterification bonds, initially considered labile, are increasingly recognized as physiologically relevant.
  • Evidence supports esterification as a mechanism for ubiquitination in proteins lacking lysine residues.

Conclusions:

  • Esterification represents a novel and significant pathway for protein ubiquitination.
  • This mechanism expands the understanding of ubiquitin's role in cellular processes.
  • Further research is warranted to fully elucidate the mechanisms and physiological impact of esterification-mediated ubiquitination.