Propionic Anhydride

Propionic anhydride is a reactive carboxylic acid anhydride used to transfer propionyl groups to chemical compounds, making it relevant to biological chemistry and laboratory analysis. Its two acyl groups are activated by the anhydride linkage, allowing nucleophiles such as amines and hydroxyl groups to attack the carbonyl carbon; the reaction forms a propionylated product and propionic acid, often under controlled, anhydrous conditions. In biology, this reagent can modify peptides, proteins, metabolites, and other biomolecules to alter their chemical properties or improve detection during analytical workflows. Such derivatization supports studies of protein acylation, molecular structure, and biochemical composition.

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JoVE Core - Organic Chemistry

Reactions of Acid Anhydrides

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2023

The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid. The reaction of acid anhydrides involves the nucleophilic attack at one...

Preparation of Acid Anhydrides

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2025

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution. The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

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2025

Naming Acid Halides The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid. IUPAC: Ethanoic acid Ethanoyl chloride Common: Acetic acid Acetyl chloride Cyclic acid halides are named by replacing the suffix...

Research

JoVE Journal - Biology
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Complete Workflow for Analysis of Histone Post-translational Modifications Using Bottom-up Mass Spectrometry: From Histone Extraction to Data Analysis

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Cited by 227 •

2016

This protocol outlines a fully integrated workflow for characterizing histone post-translational modifications using mass spectrometry (MS). The workflow includes histone purification from cell cultures or tissues, histone derivatization and digestion, MS analysis using nano-flow liquid chromatography and instructions for data analysis. The protocol is designed for completion within 2 - 3 days.

Harvesting Murine Alveolar Macrophages and Evaluating Cellular Activation Induced by Polyanhydride Nanoparticles

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Cited by 16 •

2012

Herein, we describe protocols for harvesting murine alveolar macrophages, which are resident innate immune cells in the lung, and examining their activation in response to co-culture with polyanhydride nanoparticles.

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