Exploring the scope of indole interaction with 1,2-dicarbonyl compounds
Raheleh Ghassem Zadeh1, Varoujan Yaylayan1
1McGill University, Department of Food Science and Agricultural Chemistry, 21111 Lakeshore, Ste. Anne de Bellevue, Quebec, Canada.
Food Chemistry
|May 29, 2020
Summary
Indole can trap reactive 1,2-dicarbonyl compounds, which are toxic. This study confirms indole
Area of Science:
- Biochemistry
- Organic Chemistry
- Toxicology
Background:
- 1,2-dicarbonyl compounds are highly reactive and toxic.
- Scavenging these compounds is crucial for controlling their effects.
- Indole, derived from tryptophan, is a potential carbonyl trapping agent.
Purpose of the Study:
- To investigate the general ability of indole to scavenge various 1,2-dicarbonyl compounds.
- To assess the influence of temperature and carbon chain length on this reaction.
- To demonstrate indole's capacity to trap Strecker aldehydes in complex systems.
Main Methods:
- Model systems of indole and 1,2-dicarbonyls reacted at room temperature and 150°C.
- Analysis using ESI-qTOF-MS/MS and isotopic labeling.
- Testing in alanine/glucose and bread model systems with labeled indole.
Main Results:
- Indole effectively scavenged all tested 1,2-dicarbonyl compounds.
- Reactivity of longer-chain dicarbonyls with indole showed greater temperature dependence.
- Indole successfully trapped Strecker aldehydes in food-related models.
Conclusions:
- Indole is a versatile scavenger for toxic 1,2-dicarbonyls and Strecker aldehydes.
- The reaction's efficiency is influenced by temperature and dicarbonyl structure.
- Indole-based strategies show promise for controlling dicarbonyl toxicity.
Keywords:
2,3-butanedione2,3-pentanedione3,4-hexanedioneGlycolaldehydeGlyoxalMethylglyoxalScavenging activityTryptophan[(13)C-2]indoleisotopic labeling technique and qTOF-MS/MS analysisMore Related Videos
Related Concept Videos
01:18Intramolecular Aldol Reaction
2.9K
Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more than one nucleophilic ⍺ carbon for the base to deprotonate and form the enolates. For example, in symmetrical diketones, there are four ⍺ carbons. Hence, four types of enolates are possible when treated with a base. However, since the molecule is symmetrical, the enolates formed on either side of one carbonyl group are equivalent to those...
2.9K
01:29Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
5.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.3K
01:18β-Dicarbonyl Compounds via Crossed Claisen Condensations
3.7K
Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
3.7K
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
12.0K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.0K
01:57Preparation of Diols and Pinacol Rearrangement
4.0K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
4.0K
01:29Diels–Alder Reaction: Characteristics of Dienes
4.9K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
4.9K