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Related Concept Videos

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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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...
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Esters to Carboxylic Acids: Saponification01:25

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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...
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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

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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.
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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

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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.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Defining Substrate Specificities for Lipase and Phospholipase Candidates
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Defining Substrate Specificities for Lipase and Phospholipase Candidates

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Lipid-Based Catalysis Demonstrated by Bilayer-Enabled Ester Hydrolysis.

Shu Liu1,2, Kiran Kumar3,4, Tracey Bell1

  • 1Department of Biological Science and Integrative Nanoscience Institute, Florida State University, Tallahassee, FL 32306, USA.

Membranes
|August 28, 2024
PubMed
Summary
This summary is machine-generated.

Lipid aggregates can catalyze chemical reactions within their hydrophobic regions, mimicking biological catalysis. This study shows lipids can accelerate ester hydrolysis, opening new avenues in biochemistry and synthetic biology.

Keywords:
biochemistrycatalysisheterogeneouslipid dropletpartitioningpharmacologysynthetic biologyvesicle

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Assembly of Cell Mimicking Supported and Suspended Lipid Bilayer Models for the Study of Molecular Interactions
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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Synthetic Biology

Background:

  • Lipids are not typically viewed as catalysts in biological systems.
  • Amphiphilic compounds in aggregates show catalytic activity in synthetic chemistry.
  • Lipid bilayers offer hydrophobic environments suitable for chemical reactions.

Purpose of the Study:

  • To demonstrate that lipid aggregates can provide a catalytic environment for chemical reactions.
  • To explore the potential of lipid bilayers in accelerating biochemical processes.
  • To investigate the ester hydrolysis of calcein-AM using lipid-based systems.

Main Methods:

  • Utilized a two-phase octanol-water system with cationic amphiphiles (CTAB, octadecylamine).
  • Replaced octanol with phospholipid vesicles in an aqueous environment.
  • Monitored reaction kinetics using quantitative fluorescence and characterized products with 1H-NMR.

Main Results:

  • Lipid aggregates and phospholipid vesicles successfully catalyzed the ester hydrolysis of calcein-AM.
  • Observed catalytic turnover numbers in the range of 10^-7 to 10^-8 s^-1.
  • 1H-NMR confirmed the product consistent with ester hydrolysis.

Conclusions:

  • Lipid aggregates can function as catalysts by sequestering reactants in hydrophobic microenvironments.
  • This finding has implications for understanding lipid roles in biochemistry, pharmacology, and synthetic biology.
  • Lipids represent a potential class of catalysts beyond traditional enzymatic roles.