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Mass Spectrometry: Molecular Fragmentation Overview

Mass Spectrometry: Molecular Fragmentation Overview

The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
One type of fragmentation pattern is the cleavage of a single bond in the molecular ion. The cleavage leads to a radical and a cation. The cleavage can occur at...

Mass Spectrometry: Aldehyde and Ketone Fragmentation

Mass Spectrometry: Aldehyde and Ketone Fragmentation

In mass spectrometry, the fragmentation of aliphatic aldehydes and ketones generally occurs through three key mechanisms: α-cleavage, inductive cleavage, and the McLafferty rearrangement.

Mass Spectrometry: Alcohol Fragmentation

Mass Spectrometry: Alcohol Fragmentation

Alcohols (R-OH) ionize to lose one non-bonded electron from the oxygen atom, forming molecular ions. Due to their tendency to fragment rapidly, the intensity of the molecular ion peak in the mass spectrum is weak or sometimes absent. The fragmentation patterns for alcohols occur in two ways, i.e. ⍺-cleavage and dehydration. During ⍺-cleavage, the bond at the ⍺-position adjacent to the hydroxyl group cleaves to give a resonance-stabilized cation and a radical. However, intramolecular dehydration...

Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation

Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation

The fragmentation patterns observed for compounds such as carboxylic acids, esters, and amides in the mass spectra include ⍺-cleavage and McLafferty rearrangement. Fragmentation by ⍺-cleavage preferentially occurs at the carbon-carbon bond at the ⍺-position next to the carboxylic group to generate a neutral radical and a cation. Long chain compounds with hydrogen at their γ-carbon undergo McLafferty rearrangement to give a radical cation and a neutral alkene.
For example, the fragmentation of...

Dietary Connections

Dietary Connections

In biological systems, most metabolic pathways are interconnected. The cellular respiration processes that convert glucose to ATP—such as glycolysis, pyruvate oxidation, and the citric acid cycle—tie into those that break down other organic compounds. As a result, various foods—from apples to cheese to guacamole—end up as ATP. In addition to carbohydrates, food also contains proteins and lipids—such as cholesterol and fats. All of these organic compounds are used as energy sources to produce...

Carbohydrate Digestion

Carbohydrate Digestion

Carbohydrate digestion and metabolism break down simple and complex carbohydrates from food into saccharides (i.e., sugars) for the body to use as energy. Carbohydrate digestion starts in the mouth during mastication, or chewing. The masticated carbohydrates remain intact in the stomach. Digestion resumes in the duodenum of the small intestine, where pancreatic alpha-amylase and brush border enzymes of the microvilli convert complex carbohydrates to monosaccharides. Finally, the monosaccharides...

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Updated: May 14, 2026

Determination of Glucan Chain Length Distribution of Glycogen Using the Fluorophore-Assisted Carbohydrate Electrophoresis (FACE) Method

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Fragmentation pathways during Maillard-induced carbohydrate degradation.

Mareen Smuda¹, Marcus A Glomb

¹Institute of Chemistry, Food Chemistry, Martin-Luther-University Halle-Wittenberg , Kurt-Mothes-Strasse 2, 06120 Halle/Saale, Germany.

Journal of Agricultural and Food Chemistry

|February 22, 2013

Summary

The Maillard reaction involves dicarbonyl compounds, key to browning and advanced glycation endproduct (AGE) formation. This review details five primary mechanisms of dicarbonyl decomposition in carbohydrate systems.

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Area of Science:

Food Chemistry
Medical Science
Organic Chemistry

Background:

Dicarbonyl compounds are central intermediates in the Maillard reaction, a process implicated in food browning and the formation of advanced glycation endproducts (AGEs).
These dicarbonyls, ranging from intact carbon backbones to C2-C5 fragments, are generated from various carbohydrate systems like glucose, maltose, and ascorbic acid.
The fragmentation of the original carbon skeleton is a critical step in dicarbonyl formation.

Purpose of the Study:

To review and elucidate the five major mechanisms responsible for dicarbonyl decomposition.
To provide a comprehensive overview of the chemical pathways involved in dicarbonyl fragmentation.

Main Methods:

Literature review of reported mechanisms for dicarbonyl decomposition.
Analysis of five distinct fragmentation pathways: retro-aldol fragmentation, hydrolytic α-dicarbonyl cleavage, oxidative α-dicarbonyl cleavage, hydrolytic β-dicarbonyl cleavage, and amine-induced β-dicarbonyl cleavage.

Main Results:

Identified and described five key mechanisms governing the breakdown of dicarbonyl compounds.
These mechanisms explain the origin of various dicarbonyl fragments observed in carbohydrate reactions.

Conclusions:

Understanding dicarbonyl decomposition pathways is crucial for controlling Maillard reaction products.
These fragmentation mechanisms are fundamental to both food chemistry and medical science research concerning AGEs.