Norleucine

Norleucine is a non-proteinogenic amino acid with the chemical formula C₆H₁₃NO₂. It is an isomer of the essential amino acid leucine, differing by the position of the amino group. Norleucine is not incorporated into proteins during protein synthesis in living organisms, but it is often used in scientific research as a model compound.

Structure and Properties

Norleucine is a straight-chain amino acid, classified as a non-polar, aliphatic amino acid. Its structure consists of a six-carbon chain with an amino group (NH₂) at the second carbon and a carboxyl group (COOH) at the terminal carbon. This structure is similar to that of leucine, but with a linear rather than branched side chain.

Synthesis

Norleucine can be synthesized through various chemical methods. One common method involves the hydrogenation of α-keto acids or the reductive amination of aldehydes. These synthetic routes allow for the production of norleucine in the laboratory for research purposes.

Applications in Research

Norleucine is frequently used in biochemistry and molecular biology as a standard or reference compound. It is often employed in studies of protein structure and function, particularly in mass spectrometry and chromatography techniques. Norleucine can serve as an internal standard in amino acid analysis due to its absence in natural proteins, allowing for accurate quantification of other amino acids.

Biological Significance

Although norleucine is not found in natural proteins, it can be incorporated into proteins in vitro using genetic code expansion techniques. This allows researchers to study the effects of non-canonical amino acids on protein structure and function. Norleucine's incorporation can provide insights into the flexibility and adaptability of the ribosome and the genetic code.

Safety and Handling

As with many chemical compounds, proper safety precautions should be taken when handling norleucine. It should be stored in a cool, dry place and handled with appropriate personal protective equipment to avoid ingestion, inhalation, or skin contact.

Also see

• Leucine
• Amino acid
• Protein synthesis
• Genetic code expansion
• Mass spectrometry