Canaline

Canaline

Chemical structure of L-Canaline

Canaline is a non-proteinogenic amino acid that is structurally similar to ornithine. It is primarily found in certain leguminous plants and is known for its role as a potent inhibitor of the enzyme ornithine aminotransferase.

Structure and Properties

Canaline is an analog of ornithine, differing by the presence of an oxygen atom in place of the terminal amino group. This structural modification imparts unique biochemical properties to canaline, making it a valuable tool in biochemical research.

Biosynthesis

Canaline is synthesized in plants through the modification of ornithine. The biosynthetic pathway involves the conversion of ornithine to canaline via the action of specific enzymes that introduce the oxygen atom into the molecule.

Biological Function

In plants, canaline serves as a defense compound against herbivores and pathogens. Its ability to inhibit ornithine aminotransferase disrupts the urea cycle and amino acid metabolism in organisms that consume the plant, thereby providing a protective advantage.

Inhibition of Ornithine Aminotransferase

Structure of ornithine aminotransferase complexed with canaline

Canaline is a potent inhibitor of ornithine aminotransferase, an enzyme involved in the conversion of ornithine to glutamate semialdehyde. This inhibition is due to the structural similarity between canaline and ornithine, allowing canaline to bind to the active site of the enzyme, thereby blocking its activity.

Applications in Research

Due to its inhibitory effects on ornithine aminotransferase, canaline is used in biochemical research to study the urea cycle and amino acid metabolism. It is also employed in studies investigating the role of ornithine aminotransferase in various physiological and pathological processes.

Toxicity

While canaline is beneficial to plants as a defense mechanism, it can be toxic to animals and humans if ingested in large quantities. The inhibition of ornithine aminotransferase can lead to disruptions in amino acid metabolism, which may result in adverse physiological effects.

Related Pages

• Ornithine
• Amino acid
• Urea cycle
• Enzyme inhibition