Beta-2-Thienylalanine

Beta-2-Thienylalanine is a non-proteinogenic amino acid that is used in the synthesis of peptides and proteins. It is a derivative of the essential amino acid phenylalanine, with a thienyl group replacing the phenyl group.

Structure and Properties

Beta-2-Thienylalanine has a similar structure to phenylalanine, with the key difference being the substitution of a thienyl group for the phenyl group. This results in a molecule with a slightly different set of properties, including a different pKa and hydrophobicity.

The thienyl group in Beta-2-Thienylalanine is a five-membered ring containing four carbon atoms and one sulfur atom. This gives the molecule a degree of aromaticity, which can influence its behavior in biological systems.

Synthesis

Beta-2-Thienylalanine can be synthesized from phenylalanine through a series of chemical reactions. The first step is the conversion of phenylalanine to cinnamic acid, which is then converted to thiophene through a Paal-Knorr synthesis. The thiophene is then converted to Beta-2-Thienylalanine through a series of steps involving amination and hydrogenation.

Applications

Beta-2-Thienylalanine is used in the synthesis of peptides and proteins. It can be incorporated into peptides in place of phenylalanine, resulting in peptides with altered properties. This can be useful in the development of new drugs and therapeutics.

See Also

• Amino acid
• Peptide synthesis
• Proteinogenic amino acid
• Non-proteinogenic amino acid