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MetaCyc Pathway: tyrosine degradation I

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: tyrosine fumarate catabolism

Superclasses: Degradation/Utilization/Assimilation Amino Acids Degradation Tyrosine Degradation

Some taxa known to possess this pathway include ? : Aspergillus fumigatus , Aspergillus nidulans , Homo sapiens , Pseudomonas aeruginosa , Pseudomonas fluorescens , Pseudomonas putida , Pseudomonas sp. P.J. 874 , Vibrio cholerae , Vibrio cholerae O1

Expected Taxonomic Range: Fungi , Mammalia , Proteobacteria

Summary:
This pathway of L-tyrosine degradation has been characterized in mammals, some bacteria, and the fungi Aspergillus nidulans and Aspergillus fumigatus [SanchezAmat98, FernandezCanon95, AriasBarrau04, SchmalerRipcke09] and reviewed in [Moran05] and [Penalva01]. L-Phenylalanine degradation shares this pathway after its initial hydroxylation to L-tyrosine (see MetaCyc pathway phenylalanine degradation I (aerobic)). Aspergillus nidulans also degrades phenylacetate via 2-hydroxyphenylacetate to homogentisate using this pathway [FernandezCanon95a]. The pathway ends in intermediates of central metabolism, as indicated by the pathway links. Deficiencies of enzymes in this pathway have been associated with several human genetic disorders (as indicated in the comments for the individual enzymes in this pathway). Homogentisate is a central intermediate. In addition to being further catabolized, it can also be a biosynthetic precursor for melanins (in [Denoya94]), and is used by higher plants in the biosynthesis of plastoquinone and tocopherols (in [Brownlee04] and reviewed in [Moran05]) (see MetaCyc pathways plastoquinol-9 biosynthesis I and vitamin E biosynthesis (tocopherols)).

This pathway does not occur in Escherichia coli and Salmonella, which cannot utilize L-tyrosine as a carbon and energy source (McFall, E. and Newman E. G. in [Neidhardt87]). The pathway is also lacking in the yeast Saccharomyces cerevisiae which uses a limited number of carbon sources for growth, but can use most amino acids as sole nitrogen source (in [Vuralhan05]) (see MetaCyc pathways phenylalanine degradation II (anaerobic) and phenylalanine degradation III).

A variation of this pathway has been reported in some Gram positive bacteria that can degrade L-tyrosine via 2,5-dihydroxyphenylacetate (homoprotocatechuate), rather than homogentisate, to pyruvate and succinate [Sparnins76, Blakley77]. Another variation has been shown in the gram positive bacterium Nocardia sp. 239 which can degrade L-tyrosine to homogentisate via p-hydroxyphenylpyruvate, p-hydroxyphenylacetaldehyde, and p-hydroxyphenylacetate. D- and L-phenylalanine were similarly degraded by this organism via the corresponding non-hydroxylated compounds [deBoer88a]. There is also evidence that the yeast Yarrowia lipolytica can degrade tyrosine to homogentisate through these intermediates [Carreira01]. Among the archaea, however, there is little information regarding aromatic amino acid degradation, even in the well studied hyperthermophile Pyrococcus furiosus (in [Ward02]), although a preliminary pathway has been proposed [Mai94].

Citations: [Overbeek98]

Variants: tyrosine degradation II , tyrosine degradation III , tyrosine degradation IV (to 4-methylphenol)

Relationship Links: Eawag-BBD-Pathways:PART-OF:tyr

Credits:
Revised 08-May-2006 by Fulcher CA , SRI International


References

AriasBarrau04: Arias-Barrau E, Olivera ER, Luengo JM, Fernandez C, Galan B, Garcia JL, Diaz E, Minambres B (2004). "The homogentisate pathway: a central catabolic pathway involved in the degradation of L-phenylalanine, L-tyrosine, and 3-hydroxyphenylacetate in Pseudomonas putida." J Bacteriol 186(15);5062-77. PMID: 15262943

Blakley77: Blakley ER (1977). "The catabolism of L-tyrosine by an Arthrobacter sp." Can J Microbiol 23(9);1128-39. PMID: 20216

Brownlee04: Brownlee JM, Johnson-Winters K, Harrison DH, Moran GR (2004). "Structure of the ferrous form of (4-hydroxyphenyl)pyruvate dioxygenase from Streptomyces avermitilis in complex with the therapeutic herbicide, NTBC." Biochemistry 43(21);6370-7. PMID: 15157070

Carreira01: Carreira A, Ferreira LM, Loureiro V (2001). "Brown pigments produced by Yarrowia lipolytica result from extracellular accumulation of homogentisic acid." Appl Environ Microbiol 67(8);3463-8. PMID: 11472920

deBoer88a: de Boer L, Harder W, Dijkhuizen L (1988). "Phenylalanine and tyrosine metabolism in the facultative methylotroph Nocardia sp. 239." Arch Microbiol 149:459-465.

Denoya94: Denoya CD, Skinner DD, Morgenstern MR (1994). "A Streptomyces avermitilis gene encoding a 4-hydroxyphenylpyruvic acid dioxygenase-like protein that directs the production of homogentisic acid and an ochronotic pigment in Escherichia coli." J Bacteriol 176(17);5312-9. PMID: 8071207

FernandezCanon95: Fernandez-Canon JM, Penalva MA (1995). "Fungal metabolic model for human type I hereditary tyrosinaemia." Proc Natl Acad Sci U S A 92(20);9132-6. PMID: 7568087

FernandezCanon95a: Fernandez-Canon JM, Penalva MA (1995). "Molecular characterization of a gene encoding a homogentisate dioxygenase from Aspergillus nidulans and identification of its human and plant homologues." J Biol Chem 270(36);21199-205. PMID: 7673153

Mai94: Mai X, Adams MW (1994). "Indolepyruvate ferredoxin oxidoreductase from the hyperthermophilic archaeon Pyrococcus furiosus. A new enzyme involved in peptide fermentation." J Biol Chem 269(24);16726-32. PMID: 8206994

Moran05: Moran GR (2005). "4-Hydroxyphenylpyruvate dioxygenase." Arch Biochem Biophys 433(1);117-28. PMID: 15581571

Neidhardt87: Neidhardt FC, Ingraham J, Low KB, Magasanik B, Schaechter M, Umbarger HE "Escherichia coli and Salmonella typhimurium, Cellular and Molecular Biology, Volumes 1 & 2." Microbiology, Washington, D.C., 1987.

Overbeek98: Overbeek, R, Larsen, N, Selkov, EE, Maltsev, M "The WIT Database." 1998 WWW URL http://www.cme.msu.edu/WIT/.

Penalva01: Penalva MA (2001). "A fungal perspective on human inborn errors of metabolism: alkaptonuria and beyond." Fungal Genet Biol 34(1);1-10. PMID: 11567547

SanchezAmat98: Sanchez-Amat A, Ruzafa C, Solano F (1998). "Comparative tyrosine degradation in Vibrio cholerae strains. The strain ATCC 14035 as a prokaryotic melanogenic model of homogentisate-releasing cell." Comp Biochem Physiol B Biochem Mol Biol 119(3);557-62. PMID: 9734339

SchmalerRipcke09: Schmaler-Ripcke J, Sugareva V, Gebhardt P, Winkler R, Kniemeyer O, Heinekamp T, Brakhage AA (2009). "Production of pyomelanin, a second type of melanin, via the tyrosine degradation pathway in Aspergillus fumigatus." Appl Environ Microbiol 75(2);493-503. PMID: 19028908

Sparnins76: Sparnins VL, Chapman PJ (1976). "Catabolism of L-tyrosine by the homoprotocatechuate pathway in gram-positive bacteria." J Bacteriol 127(1);362-6. PMID: 931949

Vuralhan05: Vuralhan Z, Luttik MA, Tai SL, Boer VM, Morais MA, Schipper D, Almering MJ, Kotter P, Dickinson JR, Daran JM, Pronk JT (2005). "Physiological characterization of the ARO10-dependent, broad-substrate-specificity 2-oxo acid decarboxylase activity of Saccharomyces cerevisiae." Appl Environ Microbiol 71(6);3276-84. PMID: 15933030

Ward02: Ward DE, de Vos WM, van der Oost J (2002). "Molecular analysis of the role of two aromatic aminotransferases and a broad-specificity aspartate aminotransferase in the aromatic amino acid metabolism of Pyrococcus furiosus." Archaea 1(2);133-41. PMID: 15803651

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Aarenstrup02: Aarenstrup L, Falch AM, Jakobsen KK, Neve S, Henriksen L LO, Tommerup N, Leffers H, Kristiansen K (2002). "Expression and post-translational modification of human 4-hydroxy-phenylpyruvate dioxygenase." Cell Biol Int 26(7);615-25. PMID: 12127941

Adachi66: Adachi K, Iwayama Y, Tanioka H, Takeda Y (1966). "Purification and properties of homogentisate oxygenase from Pseudomonas fluorescens." Biochim Biophys Acta 118(1);88-97. PMID: 5954067

Agsteribbe90: Agsteribbe E, van Faassen H, Hartog MV, Reversma T, Taanman JW, Pannekoek H, Evers RF, Welling GM, Berger R (1990). "Nucleotide sequence of cDNA encoding human fumarylacetoacetase." Nucleic Acids Res 18(7);1887. PMID: 2336361

Amaya04: Amaya AA, Brzezinski KT, Farrington N, Moran GR (2004). "Kinetic analysis of human homogentisate 1,2-dioxygenase." Arch Biochem Biophys 421(1);135-42. PMID: 14678794

Andersson82: Andersson SM, Pispa JP (1982). "Purification and properties of human liver tyrosine aminotransferase." Clin Chim Acta 125(2);117-23. PMID: 6128088

Awata94: Awata H, Endo F, Matsuda I (1994). "Structure of the human 4-hydroxyphenylpyruvic acid dioxygenase gene (HPD)." Genomics 23(3);534-9. PMID: 7851880

Blackburn00: Blackburn AC, Tzeng HF, Anders MW, Board PG (2000). "Discovery of a functional polymorphism in human glutathione transferase zeta by expressed sequence tag database analysis." Pharmacogenetics 10(1);49-57. PMID: 10739172

Blackburn98: Blackburn AC, Woollatt E, Sutherland GR, Board PG (1998). "Characterization and chromosome location of the gene GSTZ1 encoding the human Zeta class glutathione transferase and maleylacetoacetate isomerase." Cytogenet Cell Genet 83(1-2);109-14. PMID: 9925947

Board03: Board PG, Taylor MC, Coggan M, Parker MW, Lantum HB, Anders MW (2003). "Clarification of the role of key active site residues of glutathione transferase zeta/maleylacetoacetate isomerase by a new spectrophotometric technique." Biochem J 374(Pt 3);731-7. PMID: 12852784

Board97: Board PG, Baker RT, Chelvanayagam G, Jermiin LS (1997). "Zeta, a novel class of glutathione transferases in a range of species from plants to humans." Biochem J 328 ( Pt 3);929-35. PMID: 9396740

Bradley86: Bradley FC, Lindstedt S, Lipscomb JD, Que L, Roe AL, Rundgren M (1986). "4-Hydroxyphenylpyruvate dioxygenase is an iron-tyrosinate protein." J Biol Chem 261(25);11693-6. PMID: 3017941

Collier72: Collier RH, Kohlhaw G (1972). "Nonidentity of the aspartate and the aromatic aminotransferase components of transaminase A in Escherichia coli." J Bacteriol 1972;112(1);365-71. PMID: 4404056

Dahnhardt02: Dahnhardt D, Falk J, Appel J, van der Kooij TA, Schulz-Friedrich R, Krupinska K (2002). "The hydroxyphenylpyruvate dioxygenase from Synechocystis sp. PCC 6803 is not required for plastoquinone biosynthesis." FEBS Lett 523(1-3);177-81. PMID: 12123828

DeEknamkul87: De-Eknamkul W, Ellis BE (1987). "Purification and characterization of tyrosine aminotransferase activities from Anchusa officinalis cell cultures." Arch Biochem Biophys 257(2);430-8. PMID: 2889425

DeEknamkul87a: De-Eknamkul W, Ellis BE (1987). "Tyrosine aminotransferase: the entrypoint enzyme of the tyrosine-derived pathway in rosmarinic acid biosynthesis." Phytochemistry, 26(7), 1941-1946.

Dietrich91: Dietrich JB, Lorber B, Kern D (1991). "Expression of mammalian tyrosine aminotransferase in Saccharomyces cerevisiae and Escherichia coli. Purification to homogeneity and characterization of the enzyme overproduced in the bacteria." Eur J Biochem 201(2);399-407. PMID: 1682148

FernandezCanon96: Fernandez-Canon JM, Granadino B, Beltran-Valero de Bernabe D, Renedo M, Fernandez-Ruiz E, Penalva MA, Rodriguez de Cordoba S (1996). "The molecular basis of alkaptonuria." Nat Genet 14(1);19-24. PMID: 8782815

FernandezCanon97: Fernandez-Canon JM, Penalva MA (1997). "Spectrophotometric determination of homogentisate using Aspergillus nidulans homogentisate dioxygenase." Anal Biochem 245(2);218-21. PMID: 9056215

FernandezCanon98: Fernandez-Canon JM, Penalva MA (1998). "Characterization of a fungal maleylacetoacetate isomerase gene and identification of its human homologue." J Biol Chem 273(1);329-37. PMID: 9417084

FernandezCanon99: Fernandez-Canon JM, Hejna J, Reifsteck C, Olson S, Grompe M (1999). "Gene structure, chromosomal location, and expression pattern of maleylacetoacetate isomerase." Genomics 58(3);263-9. PMID: 10373324

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Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, biocyc12.