Mechanistic studies of choline oxidase with betaine aldehyde and its isosteric analogue 3,3-dimethylbutyraldehyde

Biochemistry

Volumn 45, Issue 6, 2006, Pages 1979-1986

  Fan, Fan ^a   Germann, Markus W ^a   Gadda, Giovanni ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; DEHYDROGENATION; ISOTOPES; PH EFFECTS; SPECTROSCOPIC ANALYSIS; SUBSTRATES;

BETAINE ALDEHYDE; CHOLINE OXIDASE; GLYCINE BETAINE;

BIOCHEMISTRY;

3,3 DIMETHYLBUTYRALDEHYDE; ALDEHYDE DEHYDROGENASE; BETAINE; CHOLINE; CHOLINE OXIDASE; GLYCINE; ISOTOPE; QUERCETIN; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; ENZYME ACTIVE SITE; ENZYME BINDING; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PH; PRIORITY JOURNAL; SPECTROPHOTOMETRY; SPECTROSCOPY; THERMODYNAMICS;

ALCOHOL OXIDOREDUCTASES; ALDEHYDES; BETAINE; BINDING SITES; CATALYSIS; FLAVINS; HYDROGEN-ION CONCENTRATION; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; OXIDATION-REDUCTION; WATER;

EID: 32444447830     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0517537     Document Type: Article

References (52)

1. Lindahl, R. (1992) Aldehyde dehydrogenases and their role in carcinogenesis, Crit. Rev. Biochem. Mol. Biol. 27, 283-335.
2. Canuto, R. A., Ferro, M., Muzio, G., Bassi, A. M., Leonarduzzi, G., Maggiora, M., Adamo, D., Poli, G., and Lindahl, R. (1994) Role of aldehyde metabolizing enzymes in mediating effects of aldehyde products of lipid peroxidation in liver cells, Carcinogenesis 15, 1359-1364.
3. Perozich, J., Nicholas, H., Wang, B. C., Lindahl, R., and Hempel, J. (1999) Relationships within the aldehyde dehydrogenase extended family, Protein Sci. 8, 137-146.
4. Perozich, J., Nicholas, H., Lindahl, R., and Hempel, J. (1999) The big book of aldehyde dehydrogenase sequences. An overview of the extended family, Adv. Exp. Med. Biol. 463, 1-7.
5. Nagai, A., and Scheidegger, A. (1991) Purification and characterization of histidinol dehydrogenase from cabbage, Arch. Biochem. Biophys. 284, 127-132.
6. Nagai, A., Ward, E., Beck, J., Tada, S., Chang, J. Y., Scheidegger, A., and Ryals, J. (1991) Structural and functional conservation of histidinol dehydrogenase between plants and microbes, Proc. Natl. Acad. Sci. U.S.A. 88, 4133-4137.
7. Hille, R. (2002) Molybdenum and tungsten in biology, Trends Biochem. Sci. 27, 360-367.
8. Hille, R. (2005) Molybdenum-containing hydroxylases, Arch. Biochem. Biophys. 433, 107-116.
9. Panoutsopoulos, G. I., and Beedham, C. (2004) Metabolism of isovanillin by aldehyde oxidase, xanthine oxidase, aldehyde dehydrogenase and liver slices, Pharmacology 73, 199-208.
10. Panoutsopoulos, G. I., Kouretas, D., and Beedham, C. (2004) Contribution of aldehyde oxidase, xanthine oxidase, and aldehyde dehydrogenase on the oxidation of aromatic aldehydes, Chem. Res. Toxicol. 17, 1368-1376.
11. Ikuta, S., Imamura, S., Misaki, H., and Horiuti, Y. (1977) Purification and characterization of choline oxidase from Arthrobacter globiformis, J. Biochem. (Tokyo) 82, 1741-1749.
12. Ikuta, S., Matuura, K., Imamura, S., Misaki, H., and Horiuti, Y. (1977) Oxidative pathway of choline to betaine in the soluble fraction prepared from Arthrobacter globiformis, J. Biochem. (Tokyo) 82, 157-163.
13. Gadda, G. (2003) Kinetic mechanism of choline oxidase from Arthrobacter globiformis, Biochim. Biophys. Acta 1646, 112-118.
14. Fan, F., Ghanem, M., and Gadda, G. (2004) Cloning, sequence analysis, and purification of choline oxidase from Arthrobacter globiformis: A bacteria enzyme involves in osmotic stress tolerance, Arch. Biochem. Biophys. 421, 149-158.
15. Gadda, G., and McAllister-Wilkins, E. E. (2003) Cloning, expression, and purification of choline dehydrogenase from the moderate halophile Halomonas elongata, Appl. Environ. Microbiol. 69, 2126-2132.
16. Gomez-Moreno, C., and Edmondson, D. E. (1985) Evidence for an aldehyde intermediate in the catalytic mechanism of thiamine oxidase, Arch. Biochem. Biophys. 239, 46.
17. Cobessi, D., Tete-Favier, F., Marchai, S., Branlant, G., and Aubry, A. (2000) Structural and biochemical investigations of the catalytic mechanism of an NADP-dependent aldehyde dehydrogenase from Streptococcus mutans, J. Mol. Biol. 300, 141-152.
18. Farres, J., Wang, T. T., Cunningham, S. J., and Weiner, H. (1995) Investigation of the active site cysteine residue of rat liver mitochondrial aldehyde dehydrogenase by site-directed mutagenesis, Biochemistry 34, 2592-2598.
19. Gonzalez-Segura, L., Velasco-Garcia, R., and Munoz-Clares, R. A. (2002) Modulation of the reactivity of the essential cysteine residue of betaine aldehyde dehydrogenase from Pseudomonas aeruginosa, Biochem. J. 361, 577-585.
20. Munoz-Clares, R. A., Gonzalez-Segura, L., Mujica-Jimenez, C., and Contreras-Diaz, L. (2003) Ligand-induced conformational changes of betaine aldehyde dehydrogenase from Pseudomonas aeruginosa and Amaranthus hypochondriacus L. leaves affecting the reactivity of the catalytic thiol, Chem.-Biol. Interact. 143-144, 129-137.
21. Wymore, T., Hempel, J., Cho, S. S., Mackerell, A. D., Jr., Nicholas, H. B., Jr., and Deerfield, D. W., II (2004) Molecular recognition of aldehydes by aldehyde dehydrogenase and mechanism of nucleophile activation, Proteins 57, 758-771.
22. Marchal, S., and Branlant, G. (1999) Evidence for the chemical activation of essential Cys-302 upon cofactor binding to non-phosphorylating glyceraldehyde 3-phosphate dehydrogenase from Streptococcus mutans, Biochemistry 38, 12950-12958.
23. Marchal, S., Cobessi, D., Rahuel-Clermont, S., Tete-Favier, F., Aubry, A., and Branlant, G. (2001) Chemical mechanism and substrate binding sites of NADP-dependent aldehyde dehydrogenase from Streptococcus mutans, Chem.-Biol. Interact. 130-132, 15-28.
24. Weiner, H., Lin, F. P., and Sanny, C. G. (1985) Chemical probes for the active site of aldehyde dehydrogenase, Prog. Clin. Biol. Res. 174, 57-70.
25. Hempel, J., Kaiser, R., and Jornvall, H. (1985) Mitochondrial aldehyde dehydrogenase from human liver. Primary structure, differences in relation to the cytosolic enzyme, and functional correlations, Eur. J. Biochem. 153, 13-28.
26. Tu, G. C., and Weiner, H. (1988) Identification of the cysteine residue in the active site of horse liver mitochondrial aldehyde dehydrogenase, J. Biol. Chem. 263, 1212-1217.
27. Hempel, J., Pietruszko, R., Fietzek, P., and Jornvall, H. (1982) Identification of a segment containing a reactive cysteine residue in human liver cytoplasmic aldehyde dehydrogenase (isoenzyme E1), Biochemistry 21, 6834-6838.
28. Teng, H., Segura, E., and Grubmeyer, C. (1993) Conserved cysteine residues of histidinol dehydrogenase are not involved in catalysis. Novel chemistry required for enzymatic aldehyde oxidation, J. Biol. Chem. 268, 14182-14188.
29. +-binding mode revealed by the crystal structure of L-histidinol dehydrogenase, Proc. Natl. Acad. Sci. U.S.A. 99, 1859-1864.
30. Corbier, C., Della Seta, F., and Branlant, G. (1992) A new chemical mechanism catalyzed by a mutated aldehyde dehydrogenase, Biochemistry 31, 12532-12535.
31. Okamoto, K., Matsumoto, K., Hille, R., Eger, B. T., Pai, E. F., and Nishino, T. (2004) The crystal structure of xanthine oxidoreductase during catalysis: implications for reaction mechanism and enzyme inhibition, Proc. Natl. Acad. Sci. U.S.A. 101, 7931-7936.
32. Choi, E. Y., Stocken, A. L., Leimkuhler, S., and Hille, R. (2004) Studies on the mechanism of action of xanthine oxidase, J. Inorg. Biochem. 98, 841-848.
33. Xia, M., Dempski, R., and Hille, R. (1999) The reductive half-reaction of xanthine oxidase. Reaction with aldehyde substrates and identification of the catalytically labile oxygen, J. Biol. Chem. 274, 3323-3330.
34. Gorham, J. (1995) Betaines in higher plants-Biosynthesis and role in stress metabolism, in Amino Acids and their Derivatives in Higher Plants (Wallsgrove, R. M., Ed.) pp 171-203, Cambridge University Press, Cambridge.
35. Vilhelmsson, O., and Miller, K. J. (2002) Humectant permeability influences growth and compatible solute uptake by Staphylococcus aureus subjected to osmotic stress, J. Food Prot. 65, 1008-1015.
36. Peddie, B. A., Wong-She, J., Randall, K., Lever, M., and Chambers, S. T. (1998) Osmoprotective properties and accumulation of betaine analogues by Staphylococcus aureus, FEMS Microbiol. Lett. 160, 25-30.
37. Peddie, B. A., Chambers, S. T., and Lever, M. (1996) Is the ability of urinary tract pathogens to accumulate glycine betaine a factor in the virulence of pathogenic strains?, J. Lab Clin. Med. 128, 417-422.
38. Alia, Hayashi, H., Sakamoto, A., and Murata, N. (1998) Enhancement of the tolerance of Arabidopsis to high temperatures by genetic engineering of the synthesis of glycinebetaine, Plant J. 16, 155-161.
39. Alia, Kondo, Y., Sakamoto, A., Nonaka, H., Hayashi, H., Saradhi, P. P., Chen, T. H., and Murata, N. (1999) Enhanced tolerance to light stress of transgenic Arabidopsis plants that express the codA gene for a bacterial choline oxidase, Plant Mol. Biol. 40, 279-288.
40. Hayashi, H., Alia, Mustardy, L., Deshnium, P., Ida, M., and Murata, N. (1997) Transformation of Arabidopsis thaliana with the codA gene for choline oxidase; accumulation of glycinebetaine and enhanced tolerance to salt and cold stress, Plant J. 12, 133-142.
41. Sakamoto, A., Valverde, R., Alia, Chen, T. H., and Murata, N. (2000) Transformation of Arabidopsis with the codA gene for choline oxidase enhances freezing tolerance of plants, Plant J. 22, 449-453.
42. Holmstrom, K. O., Somersalo, S., Mandal, A., Palva, T. E., and Welin, B. (2000) Improved tolerance to salinity and low temperature in transgenic tobacco producing glycine betaine, J. Exp. Bot. 51, 177-185.
43. Sakamoto, A., Alia, Murata, N., and Murata, A. (1998) Metabolic engineering of rice leading to biosynthesis of glycinebetaine and tolerance to salt and cold, Plant Mol. Biol. 38, 1011-1019.
44. Fan, F., and Gadda, G. (2005) On the catalytic mechanism of choline oxidase, J. Am. Chem. Soc. 127, 2067-2074.
45. Ghanem, M., and Gadda, G. (2005) On the catalytic role of the conserved active site residue His466 of choline oxidase, Biochemistry 44, 893-904.
46. Fan, F., and Gadda, G. (2005) Oxygen- and temperature-dependent kinetic isotope effects in choline oxidase: Correlating reversible hydride transfer with enviromentally enhanced tunneling, J. Am. Chem. Soc. (in press).
47. Gadda, G. (2003) pH and deuterium kinetic isotope effects studies on the oxidation of choline to betaine-aldehyde catalyzed by choline oxidase, Biochim. Biophys. Acta 1650, 4-9.
48. Gadda, G., Powell, N. L., and Menon, P. (2004) The trimethyl-ammonium headgroup of choline is a major determinant for substrate binding and specificity in choline oxidase, Arch. Biochem. Biophys. 430, 264-273.
49. Ghanem, M., Fan, F., Francis, K., and Gadda, G. (2003) Spectroscopic and kinetic properties of recombinant choline oxidase from Arthrobacter globiformis, Biochemistry 42, 15179-15188.
50. Bell, R. P. (1966) The reservible hydration of carbonyl compounds, Adv. Phys. Org. Chem. 4, 1-29.
51. Wiseman, J. S., and Abeles, R. H. (1979) Mechanism of inhibition of aldehyde dehydrogenase by cyclopropranone hydrate and the mushroom toxin coprine, Biochemistry 18, 427-435.
52. Cleland, W. W. (1982) The use of pH studies to determine chemical mechanisms of enzyme-catalyzed reactions, in Methods in Enzymology (Purich, D. L., Ed.) pp 390-405, Academic Press, New York.