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Related Concept Videos

2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
Rate-Determining Steps03:08

Rate-Determining Steps

Relating Reaction Mechanisms
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...
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.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems01:15

Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems

Oxidative reactions are pivotal in metabolizing numerous compounds, including pharmaceutical drugs. These reactions often occur in carbon-heteroatom systems, such as carbon-nitrogen, carbon-sulfur, and carbon-oxygen.
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

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Chemical model systems for cellular nitros(yl)ation reactions.

Andreas Daiber1, Stefan Schildknecht, Johanna Müller

  • 1Second Medical Clinic, Department of Cardiology, Johannes Gutenberg University, 55101 Mainz, Germany. andreas.daiber@bioredox.com

Free Radical Biology & Medicine
|May 30, 2009
PubMed
Summary

New models for protein S-nitrosylation, a key redox modification, were developed. The study suggests a 3:1 ratio of nitric oxide (NO) to superoxide (O2-) is optimal for this process, challenging existing theories.

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Area of Science:

  • Biochemistry
  • Chemical Biology
  • Posttranslational Modifications

Background:

  • S-nitrosylation is a critical redox-based protein modification.
  • The precise chemical mechanisms underlying S-nitrosylation are debated, with current models focusing on nitric oxide (NO) autoxidation or peroxynitrite intermediates.
  • Previous model systems for studying S-nitrosylation have limitations.

Purpose of the Study:

  • To propose and validate novel experimental systems for S-nitrosylation.
  • To investigate the optimal conditions and reactive species involved in S-nitrosylation.
  • To elucidate the chemical pathways of S-nitrosylation under controlled flux conditions.

Main Methods:

  • Developed two new model systems based on the thermal decomposition of 3-morpholinosydnonimine to generate controlled fluxes of nitric oxide (NO) and superoxide (O2-).
  • Modulated NO and O2- fluxes using NO donors and Cu,Zn superoxide dismutase.
  • Employed NADP+-dependent isocitrate dehydrogenase and glutathione as substrates for S-nitrosylation.
  • Utilized phenol and diaminonaphthalene to explore C- and N-nitrosation pathways.

Main Results:

  • Optimal S-nitrosylation of isocitrate dehydrogenase and glutathione occurred at nanomolar fluxes of NO and O2- in a 3:1 ratio.
  • The proposed 3:1 NO/O2- flux system was more efficient for S-nitrosylation than peroxynitrite or NO autoxidation.
  • Phenol and diaminonaphthalene indicated the involvement of multiple nitrosylation pathways.
  • Hypothetical mechanisms involving nitrosonium (NO+) or dinitrogen trioxide (N2O3) were proposed.

Conclusions:

  • A 3:1 ratio of nitric oxide (NO) to superoxide (O2-) flux represents an efficient system for S-nitrosylation.
  • This finding challenges the predominant roles of peroxynitrite and NO autoxidation in S-nitrosylation.
  • The study provides a refined model for understanding biological S-nitrosylation, potentially involving electrophilic species or transnitrosation.