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 → Proteinogenic Amino Acids Degradation → L-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
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 L-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 L-phenylalanine degradation II (anaerobic) and L-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 [deBoer88]. 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].
Relationship Links: Eawag-BBD-Pathways:PART-OF:tyr
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
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
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
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
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.
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
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
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
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
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
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
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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