Α-Methylphenylalanine

An amino acid derivative

α-Methylphenylalanine is a synthetic derivative of the amino acid phenylalanine. It is characterized by the addition of a methyl group to the alpha carbon of the phenylalanine molecule. This modification alters the properties of the amino acid, making it of interest in various biochemical and pharmacological studies.

Structure and Properties

α-Methylphenylalanine structure

α-Methylphenylalanine has a chemical structure similar to that of phenylalanine, with the primary difference being the presence of a methyl group attached to the alpha carbon. This structural change can influence the molecule's interaction with enzymes and receptors in the body.

The molecular formula of α-Methylphenylalanine is C10H13NO2, and it has a molar mass of 179.22 g/mol. The presence of the methyl group can affect the molecule's solubility, stability, and reactivity compared to its parent compound, phenylalanine.

Synthesis

The synthesis of α-Methylphenylalanine typically involves the alkylation of phenylalanine using a suitable methylating agent. This process requires careful control of reaction conditions to ensure the selective addition of the methyl group to the alpha carbon.

Biological Activity

α-Methylphenylalanine is not a naturally occurring amino acid and is not incorporated into proteins during protein synthesis. However, its structural similarity to phenylalanine allows it to interact with certain enzymes and transporters in the body. This can make it a useful tool in studying the metabolism and transport of amino acids.

Applications

In research, α-Methylphenylalanine is used to investigate the role of phenylalanine in various biological processes. It can serve as a competitive inhibitor in studies of phenylalanine metabolism, helping to elucidate the function of enzymes such as phenylalanine hydroxylase.

Additionally, α-Methylphenylalanine may be used in the development of pharmaceuticals, particularly in the design of drugs that target amino acid transporters or enzymes involved in amino acid metabolism.

Related Compounds

• Phenylalanine
• Tyrosine
• DOPA

Related Pages

• Amino acid
• Protein synthesis
• Enzyme inhibition