Phenylglycine

Phenylglycine
Names
	IUPAC name 2-Amino-2-phenylacetic acid
	Other names 2-Phenylglycine; Aminophenylacetic acid
Identifiers
CAS Number	2835-06-5 (D/L) ; 875-74-1 (D); 2935-35-5 (L);
3D model (JSmol)	Interactive image;
Beilstein Reference	608018
ChEBI	CHEBI:55484; CHEBI:439819 (L);
ChEMBL	ChEMBL131226; ChEMBL378605 (L);
ChemSpider	3732;
ECHA InfoCard	100.018.735
EC Number	200-719-1 220-608-1;
KEGG	C18623 (L);
PubChem CID	3866 (D/L); 99291 (L);
UNII	96S7ZZ1KHE ;
CompTox Dashboard (EPA)	DTXSID70862455 ;
	InChI 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;
	SMILES C1=CC=C(C=C1)C(C(=O)O)N;
Properties
Chemical formula	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). 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 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]

References

^ 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.
^ Robert E. Steiger (1942). "dl-α-Aminophenylacetic Acid". Org. Synth. 22: 23. doi:10.15227/orgsyn.022.0023.
^ 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.
^ 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.

[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.

[1]

[2]

[3]

[4]

Preparation

Ester

See also

References