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Phase II Reactions: Acetylation Reactions

Phase II Reactions: Acetylation Reactions

Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...

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 amide...

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

Physical Properties of Amines

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

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Updated: Jul 15, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

Arylamine N-acetyltransferases.

Edith Sim¹, Isaac Westwood, Elizabeth Fullam

¹University of Oxford, Department of Pharmacology, Mansfield Road, Oxford, UK. edith.sim@pharm.ox.ac.uk

Expert Opinion on Drug Metabolism & Toxicology

|April 13, 2007

Summary

Arylamine N-acetyltransferases (NATs) are crucial drug-metabolizing enzymes. Recent research reveals their new roles in human evolution, cell biology, cancer, and drug discovery, offering novel therapeutic targets.

Area of Science:

Biochemistry
Molecular Biology
Pharmacology

Background:

Arylamine N-acetyltransferases (NATs) are historically recognized as drug- and carcinogen-metabolizing enzymes.
Their roles in cellular metabolism, carcinogenesis, and pharmacogenetics are well-established.
Past research has linked NATs to disease susceptibility and epidemiological studies.

Purpose of the Study:

To explore recent advancements in NAT research beyond their traditional roles.
To highlight emerging concepts in biology and opportunities in drug discovery stemming from NAT studies.
To present novel applications of NAT research in various scientific disciplines.

Main Methods:

Analysis of recent scientific literature on Arylamine N-acetyltransferases (NATs).

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Review of studies on NAT polymorphisms, protein synthesis/degradation, gene expression, and structural analysis.

Investigation of NAT homologues in other organisms and the use of transgenic models.

Main Results:

NAT polymorphisms serve as tools in molecular anthropology for studying human evolution.
Tracking NAT protein dynamics offers insights into cellular protein folding.
NAT gene expression studies may elucidate NAT1's role in breast cancer.
A mycobacterial NAT homologue is vital for cell-wall synthesis and survival.
Transgenic mice provide in vivo models for drug metabolism research.
NAT isoenzyme structures offer in silico tools for drug discovery.

Conclusions:

Recent NAT research expands understanding into human evolution, cell biology, and disease mechanisms.
NATs present novel targets and tools for drug discovery and development.
Interdisciplinary applications of NAT research are rapidly advancing.
Further investigation into NATs promises significant contributions to medicine and biology.