Related Experiment Video
Updated: Jul 19, 2025
06:52
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
36.0K
A Sustainable Green Enzymatic Method for Amide Bond Formation
György Orsy1, Sayeh Shahmohammadi1,2, Enikő Forró1
1Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
Molecules (Basel, Switzerland)
|August 12, 2023
Summary
This study introduces a green enzymatic method for amide synthesis using Candida antarctica lipase B and a safe solvent. The process offers high yields and simplifies purification, paving the way for industrial applications.
Area of Science:
- Biocatalysis
- Green Chemistry
- Organic Synthesis
Background:
- Amide bond formation is crucial in pharmaceuticals and materials.
- Traditional methods often involve harsh conditions and toxic reagents.
- Developing sustainable synthesis routes is an ongoing challenge.
Purpose of the Study:
- To develop a sustainable and efficient enzymatic strategy for amide synthesis.
- To utilize a green solvent and a robust biocatalyst.
- To demonstrate the broad applicability of the method.
Main Methods:
- Employing *Candida antarctica* lipase B as the biocatalyst.
- Using cyclopentyl methyl ether as a green solvent.
- Reacting various carboxylic acids with primary and secondary amines.
Main Results:
- Achieved excellent conversions and high yields for amide preparation.
- Demonstrated the synthesis of 28 diverse amides.
- Eliminated the need for extensive purification steps.
Conclusions:
- The developed enzymatic strategy is simple, efficient, and sustainable.
- This method offers a green and industrially viable alternative for direct amide synthesis.
- The use of *Candida antarctica* lipase B and cyclopentyl methyl ether facilitates eco-friendly amide production.
More Related Videos
Related Concept Videos
01:14Aldehydes and Ketones with Amines: Enamine Formation Mechanism
5.7K
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
5.7K
01:29Preparation of Amides
3.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.2K
01:16Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
4.9K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
4.9K
01:23Aldehydes and Ketones with Amines: Imine Formation Mechanism
5.7K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
5.7K
01:28Amides to Carboxylic Acids: Hydrolysis
3.4K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
3.4K
01:22Preparation of 1° Amines: Azide Synthesis
4.0K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.0K