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. 1971 Feb;121(3):425–430. doi: 10.1042/bj1210425

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

J Eagles 1, W M Laird 1, S Matai 1,*, R Self 1, R L M Synge 1, A F Drake 2,†
PMCID: PMC1176589  PMID: 5119777

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.

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Selected References

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  1. Asai M., Muroi M., Sugita N., Kawashima H., Mizuno K. Enduracidin, a new antibiotic. II. Isolation and characterization. J Antibiot (Tokyo) 1968 Feb;21(2):138–146. doi: 10.7164/antibiotics.21.138. [DOI] [PubMed] [Google Scholar]
  2. BRAZHNIKOVA M. G., KUDINOVA M. K. HYDROLYSIS OF SOME ANTIBIOTICS AND OF THEIR DECOMPOSITION PRODUCTS IN THE PRESENCE OF CATION EXCHANGE RESINS. Nature. 1963 Oct 12;200:167–168. doi: 10.1038/200167b0. [DOI] [PubMed] [Google Scholar]
  3. CROKAERT R. [Carbamoyl derivatives of amino acids of biological importance. I. Catabolism products of pyrimidines. Separation technics and determination in urine in rat and man]. Bull Soc Chim Biol (Paris) 1961;43:1317–1329. [PubMed] [Google Scholar]
  4. CROKAERT R. [Carbamoyl derivatives of amino acids of biological importance. II. N-Carbamoylaspartic acid. Separation technics and determination in urine in rat and man]. Bull Soc Chim Biol (Paris) 1961;43:1331–1338. [PubMed] [Google Scholar]
  5. Iurina M. S., Lomakina N. N., Murav'eva L. I., Spiridonova I. A. Kolichestvennoe opredelenie aminokislot v aktinoidinakh A i B. Antibiotiki. 1965 Dec;10(12):1090–1094. [PubMed] [Google Scholar]
  6. Iurina M. S., Lomakina N. N. Prevrashcheniia ANTIBIOTIKOV ANTINOIDINOVOGO KOMPLEKSA V USLOVIIAKH MIAGKOGO KISLOTNOGO GIDROLIZA. Antibiotiki. 1967 Apr;12(4):279–283. [PubMed] [Google Scholar]
  7. KARASEK M. CHANGES IN FREE AND ACETYLATED AMINO ACIDS DURING TOBACCO MOSAIC VIRUS MULTIPLICATION. Biochim Biophys Acta. 1963 Dec 13;78:644–648. doi: 10.1016/0006-3002(63)91030-8. [DOI] [PubMed] [Google Scholar]
  8. Lomakina N. N., Zenkova V. A., Bognár R., Sztaricskai F., Sheinker Iu N., Turchin K. F. Struktura aminokislot iz antibiotika ristomitsina. Aminokislota A. Antibiotiki. 1968 Aug;13(8):675–682. [PubMed] [Google Scholar]
  9. MOORE S., STEIN W. H. Chromatography of amino acids on sulfonated polystyrene resins. J Biol Chem. 1951 Oct;192(2):663–681. [PubMed] [Google Scholar]
  10. Müller P., Schütte H. R. m-Hydroxyphenylglycin und 3.5-Dihydroxyphenylglycin, zwei neue Aminosäuren aus dem Latex von Euphorbia helioscopia L. Z Naturforsch B. 1968 May;23(5):659–663. [PubMed] [Google Scholar]
  11. STARK G. R., SMYTH D. G. The use of cyanate for the determination of NH2-terminal residues in proteins. J Biol Chem. 1963 Jan;238:214–226. [PubMed] [Google Scholar]
  12. SYNGE R. L., WOOD J. C. Bound amino acids in protein-free extracts of Italian ryegrass. Biochem J. 1958 Oct;70(2):321–339. doi: 10.1042/bj0700321. [DOI] [PMC free article] [PubMed] [Google Scholar]

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