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]
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| Names | |
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| IUPAC name
2-Amino-2-phenylacetic acid
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| Other names
2-Phenylglycine; Aminophenylacetic acid
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| Identifiers | |
3D model (JSmol)
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| 608018 | |
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| ChemSpider | |
| ECHA InfoCard | 100.018.735 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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Preparation
editIt 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
editThe 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
editReferences
edit- ^ 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.