N-Carbamoyl-2-(p-hydroxyphenyl)glycine from leaves of broad bean (Vicia faba L.)

Abstract

1. dl-2-(p-Hydroxyphenyl)glycine was resolved through the bromocamphorsulphonate to give its d-isomer. The N-carbamoyl derivatives of these amino acids were synthesized. Circular-dichroism studies on these and related compounds, reported in a deposited Annex, helped to establish the optical configuration. 2. N-Carbamoyl-dl-2-(p-hydroxyphenyl)glycine was isolated from broad-bean leaves. It amounted to about 0.1% of the leaf dry matter. Racemization may or may not have occurred during the isolation. There were indications of the same compound in chicory and in savoy cabbage. Under weakly acidic conditions it was converted gradually into 5-(p-hydroxyphenyl)hydantoin. Both these compounds yielded 2-(p-hydroxyphenyl)glycine on acid hydrolysis. 3. The occurrence is discussed of 2-phenylglycine derivatives in Nature and of N-carbamoyl-amino acids and hydantoins in plants. 4. Gradient elution from anion-exchange resin with acetic acid, besides proving useful for the present work, gave useful separations of pyrrolidonecarboxylic acid and of some N-acetyl-amino acids. 5. Supplementary material (Annex 1: details of experimental work other than ultraviolet and circular-dichroism spectra; Annex 2: ultraviolet absorption and circular dichroism of d-2-phenylglycine and some related compounds) has been deposited as Supplementary Publication SUP 50003 at the National Lending Library for Science and Technology, Boston Spa, Yorks. LS23 7BQ, U.K., from whom copies can be obtained on the terms indicated in Biochem. J. (1971), 121, 7.