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Related Concept Videos

Phase II Reactions: Acetylation Reactions01:24

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...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

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Single-Step Enrichment of a TAP-Tagged Histone Deacetylase of the Filamentous Fungus Aspergillus nidulans for Enzymatic Activity Assay
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Single-Step Enrichment of a TAP-Tagged Histone Deacetylase of the Filamentous Fungus Aspergillus nidulans for Enzymatic Activity Assay

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Deacetyl- tenuazonic acid.

David Siegel1, Matthias Koch, Franziska Emmerling

  • 1Bundesanstalt für Materialforschung und -prüfung, Abteilung Analytische Chemie; Referenzmaterialien, Richard-Willstätter-Strasse 11, D-12489 Berlin-Adlershof, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study details the planar heterocyclic structure of (5S)-5-[(1S)-1-methyl-prop-yl]pyrrolidine-2,4-dione. Crystal analysis reveals stabilization through specific N-H⋯O hydrogen bonding interactions.

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

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

Published on: November 23, 2016

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Structural Chemistry

Background:

  • Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
  • Heterocyclic compounds, particularly those containing nitrogen and oxygen, are fundamental building blocks in medicinal chemistry and materials science.

Purpose of the Study:

  • To elucidate the precise crystal structure of the novel compound (5S)-5-[(1S)-1-methyl-prop-yl]pyrrolidine-2,4-dione.
  • To investigate the intermolecular interactions, specifically hydrogen bonding, that stabilize the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
  • Analysis of the crystal structure included calculating the root-mean-square (r.m.s.) deviation of non-hydrogen atoms to assess planarity.
  • Identification and analysis of hydrogen bonding networks within the crystal structure.

Main Results:

  • The core heterocycle, (5S)-5-[(1S)-1-methyl-prop-yl]pyrrolidine-2,4-dione, was confirmed to be planar, with an r.m.s. deviation of 0.008 Å for all non-hydrogen atoms.
  • The crystal structure is significantly stabilized by intermolecular N-H⋯O hydrogen bonds.
  • The specific stereochemistry (5S and 1S) of the chiral centers was established.

Conclusions:

  • The planar nature of the pyrrolidine-2,4-dione ring in this compound is a key structural feature.
  • N-H⋯O hydrogen bonding plays a critical role in the self-assembly and stability of the crystal.
  • This structural information provides a foundation for further studies on the compound's physical and chemical properties.