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Amides to Carboxylic Acids: Hydrolysis

Amides to Carboxylic Acids: Hydrolysis

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...

Nitriles to Carboxylic Acids: Hydrolysis

Nitriles to Carboxylic Acids: Hydrolysis

Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

Preparation of Amides

Preparation of Amides

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...

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

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...

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Updated: Mar 26, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

DNA-Catalyzed Amide Hydrolysis.

Cong Zhou¹, Joshua L Avins¹, Paul C Klauser¹

¹Department of Chemistry, University of Illinois at Urbana-Champaign , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.

Journal of the American Chemical Society

|February 9, 2016

Summary

This summary is machine-generated.

Researchers developed new DNA catalysts (deoxyribozymes) for amide hydrolysis by incorporating protein-like functional groups. This breakthrough enables the creation of artificial proteases for novel biochemical applications.

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Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes

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Published on: July 6, 2016

Area of Science:

Biochemistry
Molecular Biology
Synthetic Biology

Background:

DNA catalysts, or deoxyribozymes, are powerful tools for various chemical reactions.
Identifying deoxyribozymes for amide hydrolysis has been challenging, with previous attempts yielding different catalytic activities.

Purpose of the Study:

To develop deoxyribozymes capable of catalyzing aliphatic amide hydrolysis.
To explore the use of modified nucleotides with protein-like functional groups to expand deoxyribozyme capabilities.

Main Methods:

In vitro selection was employed to identify novel deoxyribozymes.
Modified nucleotides bearing primary amino, carboxyl, or primary hydroxyl groups were incorporated into DNA sequences.
Selection strategies were designed to specifically target amide hydrolysis over phosphodiester hydrolysis.

Main Results:

The incorporation of modified nucleotides successfully enabled the identification of amide-hydrolyzing deoxyribozymes.
One identified deoxyribozyme retained significant catalytic activity even without the nucleotide modifications.
The study demonstrated the effectiveness of protein-like functional groups in discovering new catalytic functions for deoxyribozymes.

Conclusions:

Modified nucleotides with protein-like functional groups are crucial for identifying amide-hydrolyzing deoxyribozymes.
These findings highlight the potential of deoxyribozymes as artificial proteases for future applications.
The strategy of incorporating functional groups can be applied to discover other novel deoxyribozyme activities.