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Related Concept Videos

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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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Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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Amino Acid Catabolism01:18

Amino Acid Catabolism

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Microorganisms rely on proteins as an essential carbon and energy source, particularly in environments with limited polysaccharides or lipids. However, proteins are too large to cross the plasma membrane unaided, necessitating enzymatic degradation. Microbes secrete extracellular proteases and peptidases that hydrolyze proteins into peptides, which can then be transported across the membrane. Once inside the cell, intracellular proteases degrade these peptides into free amino acids, which...
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Phase II Reactions: Acetylation Reactions01:24

Phase II Reactions: Acetylation Reactions

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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...
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Drug Metabolism: Phase II Reactions01:14

Drug Metabolism: Phase II Reactions

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Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...
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Related Experiment Video

Updated: Mar 12, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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Late Stage Azidation of Complex Molecules.

Rashad R Karimov1, Ankit Sharma1, John F Hartwig1

  • 1Department of Chemistry, University of California at Berkeley , Berkeley, California 94720, United States.

ACS Central Science
|November 2, 2016
PubMed
Summary

This study introduces a novel iron-catalyzed method for site-selective azidation of C-H bonds and olefins in complex molecules. This approach enables the synthesis of diverse nitrogen-containing natural product derivatives.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Selective functionalization of complex molecules is key to modifying pharmacological properties.
  • Natural products and their derivatives are valuable scaffolds for drug discovery.

Purpose of the Study:

  • To develop a site-selective azidation method for complex scaffolds.
  • To synthesize novel natural product derivatives containing fluorine and azide groups.

Main Methods:

  • Utilized iron(II) acetate (Fe(OAc)2) and a PyBox ligand for catalysis.
  • Investigated site-selective azidation of benzylic and aliphatic C-H bonds.
  • Explored trifluoromethyl azidation of olefins.

Main Results:

  • Achieved site-selective azidation of C-H bonds and olefins with high regioselectivity.
  • Demonstrated tolerance of a wide range of functional groups.
  • Synthesized diverse nitrogen-containing compounds, including amines, amides, and triazoles.

Conclusions:

  • The developed catalytic system provides a versatile route for functionalizing complex molecules.
  • This method expands the toolkit for creating novel bioactive compounds from natural products.