Transition metal-catalyzed nonoxidative decarboxylation reactions

Biochemistry

Volumn 45, Issue 35, 2006, Pages 10407-10411

  Liu, Aimin ^a   Zhang, Hong ^b  

^a UNIVERSITY OF MISSISSIPPI MEDICAL CENTER   (United States)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOLOGICAL ORGANS; CATALYSTS; CHARACTERIZATION; CONFORMATIONS; ENZYMES; METABOLISM; SUBSTRATES; TRANSITION METALS;

DECARBOXYLASES; DECARBOXYLATION; HYDRATASES; ORGANIC COFACTOR;

ENZYME KINETICS;

5 CARBOXYVANILLIC ACID DECARBOXYLASE; ALPHA AMINO BETA CARBOXYMUCONATE EPSILON SEMIALDEHYDE DECARBOXYLASE; BENZOIC ACID DERIVATIVE; CARBOXYLYASE; GAMMA OXALOMESACONATE HYDRATASE; GAMMA RESORCYLATE DECARBOXYLASE; HYDROLYASE; ISOOROTATE DECARBOXYLASE; OXYGEN; THYMIDINE; TRANSITION ELEMENT; TRYPTOPHAN; UNCLASSIFIED DRUG;

ALPHA CHAIN; ARTICLE; BETA CHAIN; BIODEGRADATION; CATABOLISM; CATALYSIS; DECARBOXYLATION; ENZYME ACTIVE SITE; ENZYME ANALYSIS; ENZYME MECHANISM; ENZYME SPECIFICITY; EVOLUTION; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN FOLDING; SEQUENCE ANALYSIS; STRUCTURE ANALYSIS;

BINDING SITES; CARBOXY-LYASES; CATALYSIS; COENZYMES; CRYSTALLOGRAPHY, X-RAY; DECARBOXYLATION; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PHYLOGENY; PROTEIN STRUCTURE, SECONDARY; PSEUDOMONAS FLUORESCENS; SEQUENCE HOMOLOGY, AMINO ACID; TRANSITION ELEMENTS;

EID: 33748257672     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi061031v     Document Type: Article

References (24)

1. Ochoa, S. (1951) Biological mechanisms of carboxylation and decarboxylation, Physiol. Rev. 56, 56-106.
2. Wise, E. L., Yew, W. S., Akana, J., Gerlt, J. A., and Rayment, I. (2005) Evolution of enzymatic activities in the orotidine 5-monophosphate decarboxylase suprafamily: structural basis for catalytic promiscuity in wild-type and designed mutants of 3-keto-L-gulonate 6-phosphate decarboxylase, Biochemistry 44, 1816-1823.
3. Stanley, T. M., Johnson, W. H. J., Burks, E. A., Whitman, C. P., Hwang, C. C., and Cook, P. F. (2000) Expression and stereochemical and isotope effect studies of active 4-oxalocrotonate decarboxylase, Biochemistry 39, 718-726.
4. Li, T., Walker, A. L., Iwaki, H., Hasegawa, Y., and Liu, A. (2005) Kinetic and spectroscopic characterization of ACMSD from Pseudomonas fluorescens reveals a pentacoordinate mononuclear metallocofactor, J. Am. Chem. Soc. 127, 12282-12290.
5. Li, T., Iwaki, H., Fu, R., Hasegawa, Y., Zhang, H., and Liu, A. (2006) α-Amino-β-carboxymuconic-ε-semialdehyde decarboxylase (ACMSD) is a new member of the amidohydrolase superfamily, Biochemistry 45, 6628-6634.
6. Martynowski, D., Eyobo, Y., Li, T., Yang, K., Liu, A., and Zhang, H. (2006) Crystal Structure of α-amino-β-carboxymuconic-ε- semialdehyde decarboxylase (ACMSD): insight into the active site and catalytic mechanism of a novel decarboxylation reaction, Biochemistry 45, 10412-10421.
7. Seibert, C. M., and Raushel, F. M. (2005) Structural and catalytic diversity within the amidohydrolase superfamily, Biochemistry 44, 6383-6391.
8. Bateman, A., Coin, L., Durbin, R., Finn, R. D., Hollich, V., Griffiths-Jones, S., Khanna, A., Marshall, M., Moxon, S., Sonnhammer, E. L., Studholme, D. J., Yeats, C., and Eddy, S. R. (2004) The Pfam protein families database, Nucleic Acids Res. 32, D138-D141.
9. Holm, L., and Sander, C. (1997) An evolutionary treasure: unification of a broad set of amidohydrolases related to urease, Proteins 28, 72-82.
10. Muraki, T., Taki, M., Hasegawa, Y., Iwaki, H., and Lau, P. C. (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.
11. Tanabe, A., Egashira, Y., Fukuoka, S., Shibata, K., and Sanada, H. (2002) Purification and molecular cloning of rat 2-amino-3-carboxymuconate-6- semialdehyde decarboxylase, Biochem. J. 361, 567-575.
12. Fukuoka, S., Ishiguro, K., Yanagihara, K., Tanabe, A., Egashira, Y., Sanada, H., and Shibata, K. (2002) Identification and expression of a cDNA encoding human α-amino-β-carboxymuconic-ε-semialdehyde decarboxylase (ACMSD). A key enzyme for the tryptophan-niacine pathway and "quinolinate hypothesis", J. Biol. Chem. 277, 35162-35167.
13. Yoshida, M., Fukuhara, N., and Oikawa, T. (2004) Thermophilic, reversible γ-resorcylate decarboxylase from Rhizobium sp. strain MTP-10005: purification, molecular characterization, and expression, J. Bacteriol. 186, 6855-6863.
14. Palmatier, R. D., McCroskey, R. P., and Abbott, M. T. (1970) The enzymatic conversion of uracil 5-carboxylic acid to uracil and carbon dioxide, J. Biol. Chem. 245, 6706-6710.
15. Smiley, J. A., Kundracik, M., Landfried, D. A., Barnes, V. R., Sr., and Axhemi, A. A. (2005) Genes of the thymidine salvage pathway: thymine-7-hydroxylase from a Rhodotorula glutinis cDNA library and iso-orotate decarboxylase from Neurospora crassa, Biochim. Biophys. Acta 1723, 256-264.
16. Peng, X., Masai, E., Kitayama, H., Harada, K., Katayama, Y., and Fukuda, M. (2002) Characterization of the 5-carboxyvanillate decarboxylase gene and its role in lignin-related biphenyl catabolism in Sphingomonas paucimobilis SYK-6, Appl. Environ. Microbiol. 68, 4407-4415.
17. Peng, X., Masai, E., Kasai, D., Miyauchi, K., Katayama, Y., and Fukuda, M. (2005) A second 5-carboxyvanillate decarboxylase gene, ligW2, is important for lignin-related biphenyl catabolism in Sphingomonas paucimobilis SYK-6, Appl. Environ. Microbiol. 71, 5014-5021.
18. Hara, H., Masai, E., Katayama, Y., and Fukuda, M. (2000) The 4-oxalomesaconate hydratase gene, involved in the protocatechuate 4,5-cleavage pathway, is essential to vanillate and syringate degradation in Sphingomonas paucimobilis SYK-6, J. Bacteriol. 182, 6950-6957.
19. Maruyama, K. (1985) Purification and properties of γ- oxalomesaconate hydratase from Pseudomonas ochraceae grown with phthalate, Biochem. Biophys. Res. Commun. 128, 271-277.
20. Hasegawa, Y., Muraki, T., Tokuyama, T., Iwaki, H., Tatsuno, M., and Lau, P. C. (2000) A novel degradative pathway of 2-nitrobenzoate via 3-hydroxyanthranilate in Pseudomonas fluorescens strain KU-7, FEMS Microbiol. Lett. 190, 185-190.
21. Tanabe, A., Egashira, Y., Fukuoka, S., Shibata, K., and Sanada, H. (2002) Expression of rat hepatic 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase is affected by a high protein diet and by streptozotocin-induced diabetes, J. Nutr. 132, 1153-1159.
22. Colabroy, K. L., and Begley, T. P. (2005) Tryptophan catabolism: identification and characterization of a new degradative pathway, J. Bacteriol. 187, 7866-7869.
23. Pei, J., Sadreyev, R., and Grishin, N. V. (2003) PCMA: fast and accurate multiple sequence alignment based on profile consistency, Bioinformatics 19, 427-428.
24. Bruno, W. J., Socci, N. D., and Halpern, A. L. (2000) Weighted neighbor joining: a likelihood-based approach to distance-based phylogeny reconstruction, Mol. Biol. Evol. 17, 189-197.