Norleucine

Norleucine

Structural formula of L-Norleucine

Norleucine is a non-proteinogenic amino acid with the chemical formula C_H__NO_. It is an isomer of the amino acid leucine, differing by the position of the methyl group. Norleucine is not incorporated into proteins during translation but is used in various biochemical studies and industrial applications.

Structure and Properties

Norleucine is a straight-chain amino acid, which means it has a linear aliphatic side chain. The structure of norleucine is similar to that of leucine, but with the methyl group located at the end of the chain rather than on the second carbon. This gives norleucine the systematic name 2-aminohexanoic acid.

The presence of the amino group (NH_) and the carboxyl group (COOH) makes norleucine an amphoteric compound, capable of acting as both an acid and a base. It is a white crystalline solid at room temperature and is soluble in water.

Biological Role

Norleucine is not one of the 20 standard amino acids encoded by the genetic code. However, it is often used in biochemistry as a standard for chromatography and as an internal standard in mass spectrometry.

In some organisms, norleucine can be incorporated into proteins in place of methionine, especially under conditions where methionine is scarce. This substitution can affect the function and stability of the protein.

Industrial and Research Applications

Norleucine is used in the synthesis of peptides and as a precursor in the production of various pharmaceuticals. It is also employed in the study of enzyme mechanisms and protein structure.

In research, norleucine is used as a tool to investigate the ribosome's ability to discriminate between different amino acids during protein synthesis. It is also used in studies of protein folding and stability.

Related Compounds

• Leucine
• Isoleucine
• Methionine

Related Pages

• Amino acid
• Protein synthesis
• Biochemistry