Phenylglycine Explained

Phenylglycine is the organic compound with the formula C₆H₅CH(NH₂)CO₂H. It is a non-proteinogenic alpha amino acid related to alanine, but with a phenyl group in place of the methyl group. It is a white solid. The compound exhibits some biological activity.^[1]

Preparation

It is prepared from benzaldehyde by amino cyanation (Strecker synthesis).^[2] It can also be prepared from glyoxal^[3] and by reductive amination of phenylglyoxylic acid.

Ester

The ester methyl α‐phenylglycinate is used to convert carboxylic acids into homologated unsaturated ketones. These reactions proceed via cyclization of phenylglycinamides to oxazolones, which can be reductively cleaved with chromous reagents.^[4]

See also

• N-Phenylglycine
• (RS)-MCPG

References

1. Phenylglycine derivatives as antagonists of metabotropic glutamate receptors. 10.1016/0165-6147(94)90028-0. 7992387. Watkins, Jeff . Collingridge, Graham . Trends in Pharmacological Sciences. 1994. 15. 9. 333–42.
2. dl-α-Aminophenylacetic Acid. Robert E. Steiger. Org. Synth. . 1942. 22. 23. 10.15227/orgsyn.022.0023.
3. Asymmetric synthesis of α-amino acids from a chiral masked form of glyoxal. Agami, Claude . Couty, Francois . Puchot-Kadouri, Cathy . Synlett. 1998. 5. 1998. 449–456. 10.1055/s-1998-1685. 196817837 .
4. Encyclopedia: Methyl α-Phenylglycinate. Wolfgang Steglich . Stefan Jaroch. Methyl α-Phenylglycinate . 2001 . 10.1002/047084289X.rm229. Encyclopedia of Reagents for Organic Synthesis. 0-471-93623-5.