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. 1979 Dec;64(6):1032–1038. doi: 10.1104/pp.64.6.1032

Metabolism of l-Tyrosine to 4-Hydroxybenzaldehyde and 3-Bromo-4-Hydroxybenzaldehyde by Chloroplast-containing Fractions of Odonthalia floccosa (Esp.) Falk 1

Steven L Manley a,2, David J Chapman a
PMCID: PMC543186  PMID: 16661087

Abstract

The biosynthesis of 4-hydroxybenzaldehyde and 3-bromo-4-hydroxybenzaldehyde from l-[U-14C]tyrosine has been demonstrated in chloroplast-containing fractions obtained by differential and isopycnic centrifugation from the marine red alga Odonthalia floccosa. Surfactant and high speed centrifugation studies indicate that the biosynthetic pathway involves a particulate enzyme system, possibly located on the thylakoid membranes. The following scheme, based upon identification of labeled 14C-intermediates, is proposed for the formation of aldehydes: l-tyrosine → 4-hydroxyphenylpyruvic acid → 4-hydroxyphenylacetic acid → 4-hydroxymandelic acid → 4-hydroxybenzaldehyde → 3-bromo-4-hydroxybenzaldehyde.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Arnon D. I. COPPER ENZYMES IN ISOLATED CHLOROPLASTS. POLYPHENOLOXIDASE IN BETA VULGARIS. Plant Physiol. 1949 Jan;24(1):1–15. doi: 10.1104/pp.24.1.1. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Bhat S. G., Vaidyanathan C. S. Involvement of 4-hydroxymandelic acid in the degradation of mandelic acid by Pseudomonas convexa. J Bacteriol. 1976 Sep;127(3):1108–1118. doi: 10.1128/jb.127.3.1108-1118.1976. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Blakley E. R. The catabolism of L-tyrosine by an Arthrobacter sp. Can J Microbiol. 1977 Sep;23(9):1128–1139. doi: 10.1139/m77-169. [DOI] [PubMed] [Google Scholar]
  4. Crowden R. K. Biosynthesis of the polyphenolic acid metabolites of Polyporus tumulosus Cooke. Can J Microbiol. 1967 Feb;13(2):181–197. doi: 10.1139/m67-025. [DOI] [PubMed] [Google Scholar]
  5. Hager L. P., Morris D. R., Brown F. S., Eberwein H. Chloroperoxidase. II. Utilization of halogen anions. J Biol Chem. 1966 Apr 25;241(8):1769–1777. [PubMed] [Google Scholar]
  6. Jamaluddin M., Rao P. V., Vaidyanathan C. S. Involvement of the protocatechuate pathway in the metabolism of mandelic acid by Aspergillus niger. J Bacteriol. 1970 Mar;101(3):786–793. doi: 10.1128/jb.101.3.786-793.1970. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Kindl H. Biosynthesis and metabolism of hydroxyphenylacetic acids in higher plants. Eur J Biochem. 1969 Jan;7(3):340–347. doi: 10.1111/j.1432-1033.1969.tb19614.x. [DOI] [PubMed] [Google Scholar]
  8. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  9. Löffelhardt W. Formation of benzoic acid and p-hydroxybenzoic acid in the blue green alga Anacystis nidulans: a thylakoid-bound enzyme complex analogous to the chloroplast system. Z Naturforsch C. 1976 Nov-Dec;31(11-12):693–699. doi: 10.1515/znc-1976-11-1212. [DOI] [PubMed] [Google Scholar]
  10. Oldham K. G. Radiochemical enzyme assays: factors affecting their sensitivity and the selection of optimum conditions for assays. Int J Appl Radiat Isot. 1970 Jul;21(7):421–429. doi: 10.1016/0020-708x(70)90136-5. [DOI] [PubMed] [Google Scholar]
  11. Shephard D. C., Levin W. B. Biosynthesis in isolated Acetabularia chloroplasts. I. Protein amino acids. J Cell Biol. 1972 Aug;54(2):279–294. doi: 10.1083/jcb.54.2.279. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Sparnins V. L., Chapman P. J. Catabolism of L-tyrosine by the homoprotocatechuate pathway in gram-positive bacteria. J Bacteriol. 1976 Jul;127(1):362–366. doi: 10.1128/jb.127.1.362-366.1976. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Van Sumere C. F., Wolf G., Teuchy H., Kint J. A new thin-layer method for phenolic substances and coumarins. J Chromatogr. 1965 Oct;20(1):48–60. doi: 10.1016/s0021-9673(01)97365-0. [DOI] [PubMed] [Google Scholar]

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