Tryptophan catabolism: Identification and characterization of a new degradative pathway

Journal of Bacteriology

Volumn 187, Issue 22, 2005, Pages 7866-7869

  Colabroy, Keri L ^a   Begley, Tadhg P ^b  

^a MUHLENBERG COLLEGE   (United States)

^b Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 CARBOXYMUCONATE SEMIALDEHYDE DECARBOXYLASE; 2 AMINOMUCONATE; 2 AMINOMUCONATE DEAMINASE; 2 AMINOMUCONATE SEMIALDEHYDE DEHYDROGENASE; 2 KETOADIPATE; 3 AMINO 3 CARBOXYMUCONATE SEMIALDEHYDE; 3 HYDROXYANTHRANILATE 3,4 DIOXYGENASE; 4 OXALOCROTONATE; ACETIC ACID; ADIPIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ARYLFORMAMIDASE; CARBOXYLYASE; COENZYME A; CROTONIC ACID DERIVATIVE; DEAMINASE; GENOMIC DNA; GLUTARYL COENZYME A; KYNURENINASE; MUCONIC ACID; OXIDOREDUCTASE; PYRUVIC ACID; TRYPTOPHAN; TRYPTOPHAN 2,3 DIOXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GROWTH; BURKHOLDERIA CEPACIA; CATABOLISM; COMPARATIVE GENOMIC HYBRIDIZATION; CONTROLLED STUDY; DEGRADATION; ENZYME ACTIVITY; ESCHERICHIA COLI; GENE CLUSTER; GENE IDENTIFICATION; HYDROLYSIS; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; TRYPTOPHAN METABOLISM;

ACETIC ACID; BACTERIAL PROTEINS; BURKHOLDERIA CEPACIA; METABOLISM; MULTIGENE FAMILY; PYRUVIC ACID; TRYPTOPHAN;

BACTERIA (MICROORGANISMS); BURKHOLDERIA CEPACIA; ESCHERICHIA COLI; MAMMALIA;

EID: 27744448077     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.187.22.7866-7869.2005     Document Type: Article

References (29)

1. Bouknight, R. R., and H. L. Sadoff. 1975. Tryptophan catabolism in Bacillus megaterium. J. Bacteriol. 121:70-76.
2. Brown, R. R. 1994. Tryptophan metabolism: a review, p. 17-30. In W. Kochen and H. Steinhart. L-Tryptophan: current prospects in medicine and drug safety. Walter de Gruyter, New York, N.Y.
3. Bugg, T. D. H., and C. J. Winfield. 1998. Enzymatic cleavage of aromatic rings: mechanistic aspects of the catechol dioxygenases and later enzymes of bacterial oxidative cleavage pathways. Nat. Prod. Rep. 15:513-530.
4. Colabroy, K. L. 2005. Mechanistic and structural studies in tryptophan catabolism. Ph.D. thesis. Cornell University, Ithaca, N.Y.
5. Colabroy, K. L., and T. P. Begley. 2005. The pyridine ring of NAD is formed by a nonenzymatic pericyclic reaction. J. Am. Chem. Soc. 127:840-841.
6. Egashira, Y., H. Kouhashi, T. Ohta, and H. Sanada. 1996. Purification and properties of α-amino-β-carboxymuconate-ε-semialdehyde decarboxylase (ACMSD), key enzyme of niacin synthesis from tryptophan, from hog kidney. J. Nutr. Sci.Vitaminol. 42:173-183.
7. Fukuoka, S.-I., K. Ishiguro, K. Yanagihara, A. Tanabe, Y. Egashira, H. Sanada, and K. Shibata. 2002. Identification and expression of a cDNA encoding human α-amino-β-carboxymuconate-ε-semialdehyde decarboxylase (ACMSD): a key enzyme for the tryptophan-niacine pathway and "quinolinate hypothesis." J. Biol. Chem. 277:35162-35167.
8. Gholson, R. K., Y. Nishizuka, A. Ichiyama, H. Kawai, S. Nakamura, and O. Hayaishi. 1962. New intermediates in the catabolism of tryptophan in mammalian liver. J. Biol. Chem. 237:2043-2045.
9. Gholson, R. K., D. C. Sanders, and L. M. Henderson. 1959. Glutaric acid: a product of tryptophan metabolism. Biochem. Biophys. Res. Commun. 1:98-100.
10. Guillemin, G. J., S. J. Kerr, G. A. Smythe, P. J. Armati, and B. J. Brew. 1999. Kynurenine pathway metabolism in human astrocytes. Adv. Exp. Med. Biol. 467:125-131.
11. Hasegawa, Y., T. Muraki, T. Tokuyama, H. Iwaki, M. Tatsuno, and P. C. K. Lau. 2000. A novel degradative pathway of 2-nitrobenzoate via 3-hydroxyanthranilate in Pseudomonas fluorescens strain KU-7. FEMS Microbiol. Lett. 190:185-190.
12. He, Z., J. K. Davis, and J. C. Spain. 1998. Purification, characterization, and sequence analysis of 2-aminomuconic 6-semialdehyde dehydrogenase from Pseudomonas pseudoalcaligenes JS45. J. Bacteriol. 180:4591-4595.
13. He, Z., and J. C. Spain. 1998. A novel 2-aminomuconate deaminase in the nitrobenzene degradation pathway of Pseudomonas pseudoalcaligenes JS45. J. Bacteriol. 180:2502-2506.
14. He, Z., and J. C. Spain. 1997. Studies of the catabolic pathway of degradation of nitrobenzene by Pseudomonas pseudoalcaligenes JS45: removal of the amino group from 2-aminomuconic semialdehyde. Appl. Environ. Microbiol. 63:4839-4843.
15. Hurley, L. H., W. L. Lasswell, J. M. Ostrander, and R. Parry. 1979. Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthetic conversion of tyrosine to the C2- and C3-proline moieties of anthramycin, tomaymycin, and sibiromycin. Biochemistry 18:4230-4237.
16. Jones, G., and U. Keller. 1997. Biochemistry and genetics of actinomycin production. Drugs Pharm. Sci. 82:335-361.
17. Kurnasov, O., V. Goral, K. Colabroy, S. Gerdes, S. Anantha, A. Osterman, and T. P. Begley. 2003. NAD biosynthesis: identification of the tryptophan to quinolinate pathway in bacteria. Chem. Biol. 10:1195-1204.
18. Lovenberg, W., and B. E. Sobel. 1965. Rubredoxin: a new electron transfer protein from Clostridium pasteurianum. Proc. Natl. Acad. Sci. USA 54:193-199.
19. Magni, G., A. Amici, M. Emanuelli, N. Raffaelli, and S. Ruggieri. 1999. Enzymology of NAD+ synthesis. Adv. Enzymol. Relat. Areas Mol. Biol. 73:135-182.
20. Malherbe, P., C. Koehler, M. Da Prada, G. Lang, V. Kiefer, R. Schwarcz, H.-W. Lahm, and A. M. Cesura. 1994. Molecular cloning and functional expression of human 3-hydroxyanthranilic-acid dioxygenase. J. Biol. Chem. 269:13792-13797.
21. Mathur, G. P., C. Y. Ng, and L. M. Henderson. 1964. The synthesis and metabolism of DL-tryptophan-5-14C. J. Biol. Chem. 239:2184-2188.
22. Matthijs, S., C. Baysse, N. Koedam, K. A. Tehrani, L. Verheyden, H. Budzikiewicz, M. Schaefer, B. Hoorelbeke, J.-M. Meyer, H. De Greve, and P. Cornelis. 2004. The Pseudomonas siderophore quinolobactin is synthesized from xanthurenic acid, an intermediate of the kynurenine pathway. Mol. Microbiol. 52:371-384.
23. Muraki, T., M. Taki, Y. Hasegawa, H. Iwaki, and P. C K. Lau. 2003. Prokaryotic homologs of the eukaryotic 3-hydroxyanthranilate 3,4-dioxygenase and 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase in the 2-nitrobenzoate degradation pathway of Pseudomonas fluorescens strain KU-7. Appl. Environ. Microbiol. 69:1564-1572.
24. Nishizuka, Y., A. Ichiyama, R. K. Gholson, and O. Hayaishi. 1965. Metabolism of the benzene ring of tryptophan in mammalian tissues. I. Enzymic formation of glutaric acid from 3-hydroxyanthranilic acid. J. Biol. Chem. 240:733-739.
25. Nishizuka, Y., A. Ichiyama, and O. Hayaishi. 1970. Metabolism of the benzene ring of tryptophan (mammals), p. 463. In Methods in enzymology, vol. 17, pt. 1. Academic Press, New York, N.Y.
26. Stanier, R. Y., O. Hayaishi, and M. Tsuchida. 1951. The bacterial oxidation of tryptophan. I. A general survey of the pathways. J. Bacteriol. 62:355-366.
27. Suemori, A., K. Nakajima, R. Kurane, and Y. Nakamura. 1995. Degradation of aromatic amino acids by Rhodococcus erythropolis. Lett. Appl. Microbiol. 21:55-59.
28. Tanabe, A., Y. Egashira, S.-I. Fukuoka, K. Shibata, and H. Sanada. 2002. Purification and molecular cloning of rat 2-amino-3-carboxymuconate-6- semialdehyde decarboxylase. Biochem. J. 361:567-575.
29. Wang, L., H. Erlandsen, J. Haavik, P. M. Knappskog, and R. C. Stevens. 2002. Three-dimensional structure of human tryptophan hydroxylase and its implications for the biosynthesis of the neurotransmitters serotonin and melatonin. Biochemistry 41:12569-12574.