Phenylglycine

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Phenylglycine
Names
IUPAC name
2-Amino-2-phenylacetic acid
Other names
2-Phenylglycine; Aminophenylacetic acid
Identifiers
3D model (JSmol)
608018
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.735 Edit this at Wikidata
EC Number
  • 200-719-1 220-608-1
KEGG
UNII
  • InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)
    Key: ZGUNAGUHMKGQNY-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(C(=O)O)N
Properties
C8H9NO2
Molar mass 151.165 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).

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

References

  1. ^ Watkins, Jeff; Collingridge, Graham (1994). "Phenylglycine derivatives as antagonists of metabotropic glutamate receptors". Trends in Pharmacological Sciences. 15 (9): 333–42. doi:10.1016/0165-6147(94)90028-0. PMID 7992387.
  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. 1998 (5): 449–456. doi:10.1055/s-1998-1685. S2CID 196817837.
  4. ^ Wolfgang Steglich; Stefan Jaroch (2001). "Methyl α-Phenylglycinate". Methyl α-Phenylglycinate. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm229. ISBN 0-471-93623-5.
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