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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...

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: Introduction

Amines: Introduction

Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

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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...

Structure of Amines

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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.

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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: from structure to function.

Edith Sim¹, Kylie Walters, Sotiria Boukouvala

¹Department of Pharmacology, University of Oxford, Oxford, United Kingdom.

Drug Metabolism Reviews

|July 22, 2008

Summary

Arylamine N-acetyltransferases (NATs) are enzymes crucial for drug metabolism and pharmacogenetics. Studying NATs in humans and rodents reveals their roles in drug inactivation, cancer, and folate degradation, with implications for personalized medicine.

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Area of Science:

Biochemistry
Pharmacogenetics
Molecular Biology

Background:

Arylamine N-acetyltransferases (NATs) are cytosolic enzymes catalyzing acetyl group transfer from acetyl-CoA.
NATs play a significant role in pharmacogenetics, particularly in the metabolism of drugs like isoniazid.
Human NAT2 exhibits polymorphism, affecting isoniazid acetylation and inactivation.

Purpose of the Study:

To compare human and rodent NAT enzymes and genes to understand individual isoenzyme roles.
To investigate the clinical importance of NAT1 overexpression in breast cancers.
To explore the endogenous functions of human NAT1, such as folate degradation.

Main Methods:

Comparative genomics of human and rodent NAT enzymes.
Structural studies and intracellular tracking of polymorphic NAT variants.
Genome analyses to identify bacterial NAT homologues.

Main Results:

Human NAT1 is overexpressed in some breast cancers and involved in folate degradation.
Polymorphisms in human NAT2 affect isoniazid metabolism.
Bacterial NAT homologues are involved in isoniazid inactivation and cell wall synthesis.

Conclusions:

Comparative studies of NAT enzymes enhance understanding of their diverse functions.
NAT gene expression control is a promising area for investigation.
Structural and functional insights into NATs provide a basis for understanding their wide-ranging roles.