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. 1976 Oct;128(1):182–191. doi: 10.1128/jb.128.1.182-191.1976

Metabolism of DL-(+/-)-phenylalanine by Aspergillus niger.

G Kishore, M Sugumaran, C S Vaidyanathan
PMCID: PMC232842  PMID: 10273

Abstract

A fungus capable of degrading DL-phenylalanine was isolated from the soil and identified as Aspergillus niger. It was found to metabolize DL-phenylalanine by a new pathway involving 4-hydroxymandelic acid. D-Amino acid oxidase and L-phenylalanine: 2-oxoglutaric acid aminotransferase initiated the degradation of D- and L-phenylalanine, respectively. Both phenylpyruvate oxidase and phenylpyruvate decarboxylase activities could be demonstrated in the cell-free system. Phenylacetate hydroxylase, which required reduced nicotinamide adenine dinucleotide phosphate, converted phenylacetic acid to 2- and 4-hydroxyphenylacetic acid. Although 4-hydroxyphenylacetate was converted to 4-hydroxymandelate, 2-hydroxyphenylacetate was not utilized until the onset of sporulation. During sporulation, it was converted rapidly into homogentisate and oxidized to ring-cleaved products. 4-Hydroxymandelate was degraded to protocatechuate via 4-hydroxybenzoylformate, 4-hydroxybenzaldehyde, and 4-hydroxybenzoate.

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Selected References

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

  1. BYRDE R. J., HARRIS J. F., WOODCOCK D. Fungal detoxication, the metabolism of -(2-naphthyloxy)-n-alkylcarboxylic acids by Aspergillus niger. Biochem J. 1956 Sep;64(1):154–160. doi: 10.1042/bj0640154. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Cain R. B., Bilton R. F., Darrah J. A. The metabolism of aromatic acids by micro-organisms. Metabolic pathways in the fungi. Biochem J. 1968 Aug;108(5):797–828. doi: 10.1042/bj1080797. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. 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]
  4. Fellman J. H., Fujita T. S., Roth E. S. Assay, properties and tissue distribution of p-hydroxyphenylpyruvate hydroxylase. Biochim Biophys Acta. 1972 Sep 19;284(1):90–100. doi: 10.1016/0005-2744(72)90048-4. [DOI] [PubMed] [Google Scholar]
  5. GUNSALUS I. C., GUNSALUS C. F., STANIER R. Y. The enzymatic conversion of mandelic acid to benzoic acid. I. Gross fractionation of the system into soluble and particulate components. J Bacteriol. 1953 Nov;66(5):538–542. doi: 10.1128/jb.66.5.538-542.1953. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Gibson D. T. Microbial degradation of aromatic compounds. Science. 1967 Sep 13;161(3846):1093–1097. [PubMed] [Google Scholar]
  7. 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]
  8. KIRSHNER N. Pathway of noradrenaline formation from DOPA. J Biol Chem. 1957 Jun;226(2):821–825. [PubMed] [Google Scholar]
  9. Kalghatgi K. K., Nambudiri A. M., Bhat J. V., Subba Rao P. V. Degradation of L-penylalanine by Rhizoctonia solani. Indian J Biochem Biophys. 1974 Jun;11(2):116–118. [PubMed] [Google Scholar]
  10. Kishore G., Sugumaran M., Vaidyanathan C. S. p-Hydroxymandelic acid--a key intermediate in the metabolism of DL (plus or minus)-phenylalanine by Aspergillus niger. Biochem Biophys Res Commun. 1974 Feb 27;56(4):851–859. doi: 10.1016/s0006-291x(74)80266-4. [DOI] [PubMed] [Google Scholar]
  11. 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]
  12. Moore K., Rao P. V., Towers G. H. Degradation of phenylalanine and tyrosine by Sporobolomyces roseus. Biochem J. 1968 Jan;106(2):507–514. doi: 10.1042/bj1060507. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Moore K., Rao P. V., Towers G. H. Degradion of phenylalanine and tyrosine by Basidiomycetes. Life Sci. 1967 Dec 15;6(24):2629–2633. doi: 10.1016/0024-3205(67)90113-0. [DOI] [PubMed] [Google Scholar]
  14. Moore K., Towers G. H. Degradation of aromatic amino acids by fungi. I. Fate of L-phenylalanine in Schizophyllum commune. Can J Biochem. 1967 Nov;45(11):1659–1665. doi: 10.1139/o67-196. [DOI] [PubMed] [Google Scholar]
  15. NAIR P. M., VAIDYANATHAN C. S. A COLORIMETRIC METHOD FOR DETERMINATION OF PYROCATECHOL AND RELATED SUBSTANCES. Anal Biochem. 1964 Mar;7:315–321. [PubMed] [Google Scholar]
  16. Peterson J. A., Coon M. J. Enzymatic omega-oxidation. 3. Purification and properties of rubredoxin, a component of the omega-hydroxylation system of Pseudomonas oleovorans. J Biol Chem. 1968 Jan 25;243(2):329–334. [PubMed] [Google Scholar]
  17. Ramanarayanan M., Vaidyanathan C. S. Mandelate oxidase of Aspergillus niger. I. Properties of particulate D(-)-mandelate oxidase. Indian J Biochem Biophys. 1973 Dec;10(4):254–256. [PubMed] [Google Scholar]
  18. Stachow C. S., Stevenson I. L., Day D. Purification and properties of nicotinamide adenine dinucleotide phosphate-specific benzaldehyde dehydrogenase from Pseudomonas. J Biol Chem. 1967 Nov 25;242(22):5294–5300. [PubMed] [Google Scholar]

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