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MetaCyc Pathway: L-tryptophan degradation XII (Geobacillus)

Pathway diagram: L-tryptophan degradation XII (Geobacillus)

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.

Superclasses: Degradation/Utilization/Assimilation Amino Acids Degradation Proteinogenic Amino Acids Degradation L-tryptophan Degradation

Some taxa known to possess this pathway include ? : Geobacillus thermodenitrificans NG80-2

Expected Taxonomic Range: Bacteria

Geobacillus thermodenitrificans NG80-2 was isolated from a deep-subsurface oil reservoir in Northern China. This organism degrades L-tryptophan to acetyl-CoA via the intermediates anthranilate and 3-hydroxyanthranilate. While L-tryptophan degradation via 3-hydroxyanthranilate is well documented in eukaryotes (although via a different pathway, as documented in pathway L-tryptophan degradation III (eukaryotic)), this is an unusual route for bacteria [Liu10b].

The key enzyme of the pathway, which converts anthranilate to 3-hydroxyanthranilate, is anthranilate hydroxylase. The gene encoding the protein has been cloned, expressed in Escherichia coli and purified, and was shown to be an FAD-dependent hydroxylase. The GTNG_3160 gene that encodes the enzyme is found in a cluster that also contains two additional genes that encode a riboflavin kinase/FMN adenylyltransferase and an FAD reductase, which together provide FAD for the hydroxylase [Liu10b].

The anthranilate degradation gene cluster (GNTG_3150-GNTG_3164) contains genes for the downstream degradation of 3-hydroxyanthranilate via a meta-cleavage pathway, with great similarity to the genes of Pseudomonas fluorescens KU-7, encoding proteins involved in 2-nitrobenzoate degradation [Hasegawa00]. In addition, the cluster is located adjacent to a tryptophan degradation gene cluster (GNTG_3165-GNTG_3169). However, so far only the function of three of these genes has been verified experimentally (anthranilate hydroxylase, 3-hydroxyanthranilate 3,4-dioxygenase, and 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase) [Liu10b].

Transcription of the studied genes was greatly enhanced (several thousand-fold) when the cells were grown with either anthranilate or L-tryptophan as the sole carbon source (as opposed to growth with sucrose) [Liu10b].

Subpathways: 2-amino-3-carboxymuconate semialdehyde degradation to 2-oxopentenoate , anthranilate degradation IV (aerobic) , L-tryptophan degradation I (via anthranilate) , 2-oxopentenoate degradation

Variants: L-tryptophan degradation II (via pyruvate) , L-tryptophan degradation III (eukaryotic) , L-tryptophan degradation IV (via indole-3-lactate) , L-tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde , L-tryptophan degradation V (side chain pathway) , L-tryptophan degradation VI (via tryptamine) , L-tryptophan degradation VII (via indole-3-pyruvate) , L-tryptophan degradation VIII (to tryptophol) , L-tryptophan degradation IX , L-tryptophan degradation X (mammalian, via tryptamine) , L-tryptophan degradation XI (mammalian, via kynurenine)

Created 30-Apr-2010 by Caspi R , SRI International


Hasegawa00: Hasegawa Y, Muraki T, Tokuyama T, Iwaki H, Tatsuno M, Lau PC (2000). "A novel degradative pathway of 2-nitrobenzoate via 3-hydroxyanthranilate in Pseudomonas fluorescens strain KU-7." FEMS Microbiol Lett 190(2);185-90. PMID: 11034277

Liu10b: Liu X, Dong Y, Li X, Ren Y, Li Y, Wang W, Wang L, Feng L (2010). "Characterization of the anthranilate degradation pathway in Geobacillus thermodenitrificans NG80-2." Microbiology 156(Pt 2);589-95. PMID: 19942660

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

Aemprapa98: Aemprapa S, Williams PA (1998). "Implications of the xylQ gene of TOL plasmid pWW102 for the evolution of aromatic catabolic pathways." Microbiology 144 ( Pt 5);1387-96. PMID: 9611813

Austin09: Austin CJ, Astelbauer F, Kosim-Satyaputra P, Ball HJ, Willows RD, Jamie JF, Hunt NH (2009). "Mouse and human indoleamine 2,3-dioxygenase display some distinct biochemical and structural properties." Amino Acids 36(1);99-106. PMID: 18274832

Basran08: Basran J, Rafice SA, Chauhan N, Efimov I, Cheesman MR, Ghamsari L, Raven EL (2008). "A kinetic, spectroscopic, and redox study of human tryptophan 2,3-dioxygenase." Biochemistry 47(16);4752-60. PMID: 18370401

Batabyal07: Batabyal D, Yeh SR (2007). "Human tryptophan dioxygenase: a comparison to indoleamine 2,3-dioxygenase." J Am Chem Soc 129(50);15690-701. PMID: 18027945

Bouknight75: Bouknight RR, Sadoff HL (1975). "Tryptophan catabolism in Bacillus megaterium." J Bacteriol 121(1);70-6. PMID: 803956

Brady75: Brady FO (1975). "Tryptophan 2,3-dioxygenase: a review of the roles of the heme and copper cofactors in catalysis." Bioinorg Chem 5(2);167-82. PMID: 178384

BRENDA14: BRENDA team (2014). "Imported from BRENDA version existing on Aug 2014."

Brown86: Brown D, Hitchcock MJ, Katz E (1986). "Purification and characterization of kynurenine formamidase activities from Streptomyces parvulus." Can J Microbiol 32(6);465-72. PMID: 2425918

Burlingame83: Burlingame R, Chapman PJ (1983). "Stereospecificity in meta-fission catabolic pathways." J Bacteriol 155(1);424-6. PMID: 6345511

Burlingame83a: Burlingame R, Chapman PJ (1983). "Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli." J Bacteriol 1983;155(1);113-21. PMID: 6345502

Calderone02: Calderone V, Trabucco M, Menin V, Negro A, Zanotti G (2002). "Cloning of human 3-hydroxyanthranilic acid dioxygenase in Escherichia coli: characterisation of the purified enzyme and its in vitro inhibition by Zn2+." Biochim Biophys Acta 1596(2);283-92. PMID: 12007609

Clark80: Clark DP, Cronan JE (1980). "Acetaldehyde coenzyme A dehydrogenase of Escherichia coli." J Bacteriol 144(1);179-84. PMID: 6998946

Colabroy05: Colabroy KL, Begley TP (2005). "Tryptophan catabolism: identification and characterization of a new degradative pathway." J Bacteriol 187(22);7866-9. PMID: 16267312

Eaton96: Eaton RW (1996). "p-Cumate catabolic pathway in Pseudomonas putida Fl: cloning and characterization of DNA carrying the cmt operon." J Bacteriol 1996;178(5);1351-62. PMID: 8631713

Eguchi84: Eguchi N, Watanabe Y, Kawanishi K, Hashimoto Y, Hayaishi O (1984). "Inhibition of indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by beta-carboline and indole derivatives." Arch Biochem Biophys 232(2);602-9. PMID: 6431906

Ferrandez97a: Ferrandez A, Garcia JL, Diaz E (1997). "Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12." J Bacteriol 1997;179(8);2573-81. PMID: 9098055

Fischer13: Fischer B, Boutserin S, Mazon H, Collin S, Branlant G, Gruez A, Talfournier F (2013). "Catalytic properties of a bacterial acylating acetaldehyde dehydrogenase: evidence for several active oligomeric states and coenzyme A activation upon binding." Chem Biol Interact 202(1-3);70-7. PMID: 23237860

Fuchs08: Fuchs G (2008). "Anaerobic metabolism of aromatic compounds." Ann N Y Acad Sci 1125;82-99. PMID: 18378589

Fukuoka02: Fukuoka S, Ishiguro K, Yanagihara K, Tanabe A, Egashira Y, Sanada H, Shibata K (2002). "Identification and expression of a cDNA encoding human alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase (ACMSD). A key enzyme for the tryptophan-niacine pathway and "quinolinate hypothesis"." J Biol Chem 277(38);35162-7. PMID: 12140278

Gupta00: Gupta S, Mat-Jan F, Latifi M, Clark DP (2000). "Acetaldehyde dehydrogenase activity of the AdhE protein of Escherichia coli is inhibited by intermediates in ubiquinone synthesis." FEMS Microbiol Lett 182(1);51-5. PMID: 10612730

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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