2-Amino-2-phenylacetic acid

Description

2-Amino-2-phenylacetic acid is a natural compound that has been identified as a selective inhibitor of cyclooxygenase 2 (COX-2), and it exhibits antiinflammatory activity. It has been shown to inhibit COX-2 at low concentrations and to be less potent than aspirin in inhibiting COX-1. It is also an amide, with a molecular weight of 296. In order to determine the structure of it, XRD data was collected from the monosodium salt form of the compound. The ester hydrochloride form was used for enzyme activity assays because it is more soluble in water than the free base form. The synthesis of 2-Amino-2-phenylacetic acid was achieved through a two step process involving amide formation and hydrolysis.

Chemical properties

white amorphous powder

The Uses of 2-Amino-2-phenylacetic acid

DL-α-Phenylglycine is used as a reagent in the synthesis of benzoquinone-amino acid conjugates which have antibacterial activity.

Definition

ChEBI: An amino acid with a structure in which a phenyl ring is bonded to the alpha-carbon of glycine.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 84, 1955
Synthetic Communications, 2, p. 423, 1972 DOI: 10.1080/00397917208081791