Phenylglycine

Phenylglycine
Names
IUPAC name
2-Amino-2-phenylacetic acid
Other names
2-Phenylglycine; Aminophenylacetic acid
Identifiers
3D model (JSmol)
608018
ChEBI
ChEMBL
ChemSpider
EC Number 200-719-1 220-608-1
KEGG
Properties
C8H9NO2
Molar mass 151.17 g·mol−1
Appearance White solid
Melting point 290 °C (554 °F; 563 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 methyl. 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 phenylpyruvic 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

References

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