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2° Amines to N-Nitrosamines: Reaction with NaNO2

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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.

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Related Experiment Video

Updated: Jun 7, 2026

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

Published on: February 16, 2022

Chemical methods to detect S-nitrosation.

Hua Wang¹, Ming Xian

¹Department of Chemistry, Washington State University, Pullman, WA 99164, USA.

Current Opinion in Chemical Biology

|November 2, 2010

Summary

This summary is machine-generated.

Detecting S-nitrosation, a key protein modification by nitric oxide (NO), is challenging due to the instability of S-nitrosothiols (SNO). This review highlights recent advancements in methods for directly detecting S-nitrosation sites.

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Nitropeptide Profiling and Identification Illustrated by Angiotensin II

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Last Updated: Jun 7, 2026

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

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Published on: February 16, 2022

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

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Nitropeptide Profiling and Identification Illustrated by Angiotensin II

Nitropeptide Profiling and Identification Illustrated by Angiotensin II

Published on: June 16, 2019

Area of Science:

Biochemistry
Molecular Biology
Cell Signaling

Background:

Nitric oxide (NO) acts as a crucial cell-signaling molecule in physiological and pathophysiological contexts.
S-nitrosation, the modification of cysteine residues by NO, alters protein function and serves as a key post-translational modification for NO-dependent signaling.
The detection and quantification of S-nitrosation in biological samples are hindered by the inherent instability of S-nitrosothiols (SNO).

Purpose of the Study:

To review recent advancements in methodologies for detecting S-nitrosation.
To focus on methods enabling the direct conjugation and detection of S-nitrosation sites on proteins.

Main Methods:

Review of literature on S-nitrosation detection techniques.
Emphasis on methods that directly label or conjugate S-nitrosation sites.
Discussion of techniques addressing the lability of S-nitrosothiols (SNO).

Main Results:

Recent developments have improved the ability to detect S-nitrosation.
Methods focusing on direct conjugation offer promising solutions to the challenge of SNO lability.
Advancements facilitate more accurate quantification and characterization of S-nitrosated proteins.

Conclusions:

Improved methods for S-nitrosation detection are crucial for understanding NO-mediated biological processes.
Direct conjugation techniques represent a significant step forward in overcoming the challenges associated with SNO instability.
Further development in these methods will enhance the study of protein S-nitrosation in biological systems.