Choline oxidase and related systems

Oxidases, Dehydrogenases and Related Systems

Volumn , Issue , 2012, Pages 155-175

  Gadda, Giovanni ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84961829267     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (104)

1. Gadda G. Kinetic mechanism of choline oxidase from Arthrobacter globiformis. Biochim Biophys Acta 2003;1646:112-8.
2. Ikuta S, Imamura S, Misaki H, Horiuti Y. Purification and characterization of choline oxidase from Arthrobacter globiformis. J Biochem 1977;82:1741-9.
3. Gadda G. Oxygen activation in flavoprotein oxidases: the importance of being positive. Biochemistry 2012;51:2662-9.
4. Gadda G. Hydride transfer made easy in the reaction of alcohol oxidation catalyzed by flavindependent oxidases. Biochemistry 2008;47:13745-53.
5. Ribitsch D, Winkler S, Gruber K, et al. Engineering of choline oxidase from Arthrobacter nicotianae for potential use as biological bleach in detergents. Appl Microbiol Biotechnol 2010;87:1743-52.
6. Ribitsch D, Karl W, Wehrschutz-Sigl E, et al. Heterologous expression and characterization of choline oxidase from the soil bacterium Arthrobacter nicotianae. Appl Microbiol Biotechnol 2009;81:875-86.
7. Hekmat A, Saboury AA, Moosavi-Movahedi AA, Ghourchian H, Ahmad F. Effects of pH on the activity and structure of choline oxidase from Alcaligenes species. Acta Biochim Pol 2008;55:549-57.
8. Tavakoli H, Ghourchian H, Moosavi-Movahedi AA, Chilaka FC. Effects of paraoxon and ethylparathion on choline oxidase from Alcaligenes species: inhibition and denaturation. Int J Biol Macromol 2005;36:318-23.
9. Ohta-Fukuyama M, Miyake Y, Emi S, Yamano T. Identification and properties of the prosthetic group of choline oxidase from Alcaligenes sp. J Biochem 1980;88:197-203.
10. Ebisuzaki K, Williams JN, Jr. Preparation and partial purification of soluble choline dehydrogenase from liver mitochondria. Biochem J 1955;60:644-6.
11. Rendina G, Singer TP. Studies on choline dehydrogenase. I. Extraction in soluble form, assay, and some properties of the enzyme. J Biol Chem 1959;234:1605-10.
12. Barrett MC, Dawson AP. The reaction of choline dehydrogenase with some electron acceptors. Biochem J 1975;151:677-83.
13. Tsuge H, Nakano Y, Onishi H, Futamura Y, Ohashi K. A novel purification and some properties of rat liver mitochondrial choline dehydrogenase. Biochim Biophys Acta 1980;614:274-84.
14. Russell R, Scopes RK. Use of hydrophobic chromatography for purification of the membrane-located choline dehydrogenase from a Pseudomonas strain. Bioseparation 1994;4:279-84.
15. Perrino LA, Pierce SK. Choline dehydrogenase kinetics contribute to glycine betaine regulation differences in chesapeake bay and atlantic oysters. J Exp Zool 2000;286:250-61.
16. Andresen PA, Kaasen I, Styrvold OB, Boulnois G, Strom AR. Molecular cloning, physical mapping and expression of the bet genes governing the osmoregulatory choline-glycine betaine pathway of Escherichia coli. J Gen Microbiol 1988;134:1737-46.
17. Landfald B, Strom AR. Choline-glycine betaine pathway confers a high level of osmotic tolerance in Escherichia coli. J Bacteriol 1986;165:849-55.
18. Pocard JA, Vincent N, Boncompagni E, Smith LT, Poggi MC, Le Rudulier D. Molecular characterization of the bet genes encoding glycine betaine synthesis in Sinorhizobium meliloti 102F34. Microbiology 1997;143 (Pt 4):1369-79.
19. Gadda G, McAllister-Wilkins EE. Cloning, expression, and purification of choline dehydrogenase from the moderate halophile Halomonas elongata. Appl Environ Microbiol 2003;69:2126-32.
20. Cavener DR. GMC oxidoreductases. A newly defined family of homologous proteins with diverse catalytic activities. J Mol Biol 1992;223:811-4.
21. Fan F, Gadda G. On the catalytic mechanism of choline oxidase. J Am Chem Soc 2005;127:2067-74.
22. Ferreira P, Hernandez-Ortega A, Herguedas B, Martinez AT, Medina M. Aryl-alcohol oxidase involved in lignin degradation: a mechanistic study based on steady and pre-steady-state kinetics and primary and solvent isotope effects with two alcohol substrates. J Biol Chem 2009;284:24840-7.
23. Sucharitakul J, Wongnate T, Chaiyen P. Kinetic isotope effects on the noncovalent flavin mutant protein of pyranose 2-oxidase reveal insights into the flavin reduction mechanism. Biochemistry 2010;49:3753-65.
24. Ueland PM. Choline and betaine in health and disease. J Inherit Metab Dis 2011;34:3-15.
25. Lever M, Slow S. The clinical significance of betaine, an osmolyte with a key role in methyl group metabolism. Clin Biochem 2010;43:732-44.
26. Institute of Medicine, and National Academy of Sciences USA (1998) Choline. In: Dietary reference intakes for folate, thiamin, riboflavin, niacin, vitamin B12, panthothenic acid, biotin, and choline Vol 1. Washington DC: National Academy Press; 1998:309-422.
27. Zeisel SH, Blusztajn JK. Choline and human nutrition. Annu Rev Nutr 1994;14:269-96.
28. Blusztajn JK, Zeisel SH, Wurtman RJ. Developmental changes in the activity of phosphatidylethanolamine N-methyltransferases in rat brain. Biochem J 1985;232:505-11.
29. Zeisel SH. Gene response elements, genetic polymorphisms and epigenetics influence the human dietary requirement for choline. IUBMB Life 2007;59:380-7.
30. Sunden SL, Renduchintala MS, Park EI, Miklasz SD, Garrow TA. Betaine-homocysteine methyltransferase expression in porcine and human tissues and chromosomal localization of the human gene. Arch Biochem Biophys 1997;345:171-4.
31. Locker J, Reddy TV, Lombardi B. DNA methylation and hepatocarcinogenesis in rats fed a choline-devoid diet. Carcinogenesis 1986;7:1309-12.
32. Tsujiuchi T, Tsutsumi M, Sasaki Y, Takahama M, Konishi Y. Hypomethylation of CpG sites and c-myc gene overexpression in hepatocellular carcinomas, but not hyperplastic nodules, induced by a choline-deficient L-amino acid-defined diet in rats. Jpn J Cancer Res 1999;90:909-13.
33. Holliday R, Grigg GW. DNA methylation and mutation. Mutat Res 1993;285:61-7.
34. Jaenisch R. DNA methylation and imprinting: why bother? Trends Genet 1997;13:323-9.
35. Robertson KD, Jones PA. Dynamic interrelationships between DNA replication, methylation, and repair. Am J Hum Genet 1997;61:1220-4.
36. Zingg JM, Jones PA. Genetic and epigenetic aspects of DNA methylation on genome expression, evolution, mutation and carcinogenesis. Carcinogenesis 1997;18:869-82.
37. Jones PA, Gonzalgo ML. Altered DNA methylation and genome instability: a new pathway to cancer? Proc Natl Acad Sci U S A 1997;94:2103-5.
38. Niculescu MD, Craciunescu CN, Zeisel SH. Dietary choline deficiency alters global and gene-specific DNA methylation in the developing hippocampus of mouse fetal brains. FASEB J 2006;20:43-9.
39. Niculescu MD, Craciunescu CN, Zeisel SH. Gene expression profiling of choline-deprived neural precursor cells isolated from mouse brain. Brain Res Mol Brain Res 2005;134:309-22.
40. Niculescu MD, Yamamuro Y, Zeisel SH. Choline availability modulates human neuroblastoma cell proliferation and alters the methylation of the promoter region of the cyclin-dependent kinase inhibitor 3 gene. J Neurochem 2004;89:1252-9.
41. Niculescu MD, Zeisel SH. Diet, methyl donors and DNA methylation: interactions between dietary folate, methionine and choline. J Nutr 2002;132:2333S-5S.
42. Mehedint MG, Niculescu MD, Craciunescu CN, Zeisel SH. Choline deficiency alters global histone methylation and epigenetic marking at the Re1 site of the calbindin 1 gene. FASEB J 2010;24:184-95.
43. da Costa KA, Niculescu MD, Craciunescu CN, Fischer LM, Zeisel SH. Choline deficiency increases lymphocyte apoptosis and DNA damage in humans. Am J Clin Nutr 2006;84:88-94.
44. Vafai SB, Stock JB. Protein phosphatase 2A methylation: a link between elevated plasma homocysteine and Alzheimer's Disease. FEBS Lett 2002;518:1-4.
45. Pajares MA, Perez-Sala D. Betaine homocysteine S-methyltransferase: just a regulator of homocysteine metabolism? Cell Mol Life Sci 2006;63:2792-803.
46. Zeisel SH. Choline: critical role during fetal development and dietary requirements in adults. Annu Rev Nutr 2006;26:229-50.
47. Chen TH, Murata N. Glycinebetaine: an effective protectant against abiotic stress in plants. Trends Plant Sci 2008;13:499-505.
48. Graham JE, Wilkinson BJ. Staphylococcus aureus osmoregulation: roles for choline, glycine betaine, proline, and taurine. J Bacteriol 1992;174:2711-6.
49. Kunin CM, Rudy J. Effect of NaCl-induced osmotic stress on intracellular concentrations of glycine betaine and potassium in Escherichia coli, Enterococcus faecalis, and staphylococci. J Lab Clin Med 1991;118:217-24.
50. Lucht JM, Bremer E. Adaptation of Escherichia coli to high osmolarity environments: osmoregulation of the high-affinity glycine betaine transport system proU. FEMS Microbiol Rev 1994;14:3-20.
51. Peddie BA, Lever M, Randall K, Chambers ST. Osmoprotective activity, urea protection, and accumulation of hydrophilic betaines in Escherichia coli and Staphylococcus aureus. Antonie Van Leeuwenhoek 1999;75:183-9.
52. Wemekamp-Kamphuis HH, Wouters JA, Sleator RD, Gahan CG, Hill C, Abee T. Multiple deletions of the osmolyte transporters BetL, Gbu, and OpuC of Listeria monocytogenes affect virulence and growth at high osmolarity. Appl Environ Microbiol 2002;68:4710-6.
53. Price CT, Bukka A, Cynamon M, Graham JE. Glycine betaine uptake by the ProXVWZ ABC transporter contributes to the ability of Mycobacterium tuberculosis to initiate growth in human macrophages. J Bacteriol 2008;190:3955-61.
54. Ozdemir M, Arslan F, Arslan H. An amperometric biosensor for choline determination prepared from choline oxidase immobilized in polypyrrole-polyvinylsulfonate film. Artif Cells Blood Substit Immobil Biotechnol 2012.
55. Chen TH, Murata N. Glycinebetaine protects plants against abiotic stress: mechanisms and biotechnological applications. Plant Cell Environ 2011;34:1-20.
56. Khan A, Ab Ghani S. Multienzyme microbiosensor based on electropolymerized o-phenylenediamine for simultaneous in vitro determination of acetylcholine and choline. Biosens Bioelectron 2012;31:433-8.
57. Ma XJ, Wang Z, Ryan PD, et al. A two-gene expression ratio predicts clinical outcome in breast cancer patients treated with tamoxifen. Cancer Cell 2004;5:607-16.
58. Wang Z, Dahiya S, Provencher H, et al. The prognostic biomarkers HOXB13, IL17BR, and CHDH are regulated by estrogen in breast cancer. Clin Cancer Res 2007;13:6327-34.
59. Glunde K, Bhujwalla ZM, Ronen SM. Choline metabolism in malignant transformation. Nat Rev Cancer 2011;11:835-48.
60. Glunde K, Jiang L, Moestue SA, Gribbestad IS. MRS and MRSI guidance in molecular medicine: targeting and monitoring of choline and glucose metabolism in cancer. NMR Biomed 2011;24:673-90.
61. Daly PF, Lyon RC, Faustino PJ, Cohen JS. Phospholipid metabolism in cancer cells monitored by 31P NMR spectroscopy. J Biol Chem 1987;262:14875-8.
62. Aboagye EO, Bhujwalla ZM. Malignant transformation alters membrane choline phospholipid metabolism of human mammary epithelial cells. Cancer Res 1999;59:80-4.
63. Hacker HJ, Steinberg P, Bannasch P. Pyruvate kinase isoenzyme shift from L-type to M2-type is a late event in hepatocarcinogenesis induced in rats by a choline-deficient/DL-ethionine-supplemented diet. Carcinogenesis 1998;19:99-107.
64. da Costa KA, Kozyreva OG, Song J, Galanko JA, Fischer LM, Zeisel SH. Common genetic polymorphisms affect the human requirement for the nutrient choline. FASEB J 2006;20: 1336-44.
65. Xu X, Gammon MD, Zeisel SH, et al. Choline metabolism and risk of breast cancer in a population-based study. FASEB J 2008;22:2045-52.
66. Johnson AR, Lao S, Wang T, Galanko JA, Zeisel SH. Choline Dehydrogenase Polymorphism rs12676 Is a Functional Variation and Is Associated with Changes in Human Sperm Cell Function. PLoS One 2012;7:e36047.
67. Johnson AR, Craciunescu CN, Guo Z, et al. Deletion of murine choline dehydrogenase results in diminished sperm motility. FASEB J 2010;24:2752-61.
68. Quaye O, Lountos GT, Fan F, Orville AM, Gadda G. Role of Glu312 in binding and positioning of the substrate for the hydride transfer reaction in choline oxidase. Biochemistry 2008;47:243-56.
69. Fan F, Ghanem M, Gadda G. Cloning, sequence analysis, and purification of choline oxidase from Arthrobacter globiformis: a bacterial enzyme involved in osmotic stress tolerance. Arch Biochem Biophys 2004;421:149-58.
70. Fraaije MW, Mattevi A. Flavoenzymes: diverse catalysts with recurrent features. Trends Biochem Sci 2000;25:126-32.
71. Xin Y, Gadda G, Hamelberg D. The cluster of hydrophobic residues controls the entrance to the active site of choline oxidase. Biochemistry 2009;48:9599-605.
72. Orville AM, Lountos GT, Finnegan S, Gadda G, Prabhakar R. Crystallographic, spectroscopic, and computational analysis of a flavin C4a-oxygen adduct in choline oxidase. Biochemistry 2009;48:720-8.
73. Sucharitakul J, Prongjit M, Haltrich D, Chaiyen P. Detection of a C4a-hydroperoxyflavin intermediate in the reaction of a flavoprotein oxidase. Biochemistry 2008;47:8485-90.
74. Finnegan S, Yuan H, Wang YF, Orville AM, Weber IT, Gadda G. Structural and kinetic studies on the Ser101Ala variant of choline oxidase: catalysis by compromise. Arch Biochem Biophys 2010;501:207-13.
75. Baron R, Riley C, Chenprakhon P, et al. Multiple pathways guide oxygen diffusion into flavoenzyme active sites. Proc Natl Acad Sci U S A 2009;106:10603-8.
76. Finnegan S, Agniswamy J, Weber IT, Gadda G. Role of valine 464 in the flavin oxidation reaction catalyzed by choline oxidase. Biochemistry 2010;49:2952-61.
77. Ghanem M, Fan F, Francis K, Gadda G. Spectroscopic and kinetic properties of recombinant choline oxidase from Arthrobacter globiformis. Biochemistry 2003;42:15179-88.
78. Ghanem M, Gadda G. Effects of reversing the protein positive charge in the proximity of the flavin N(1) locus of choline oxidase. Biochemistry 2006;45:3437-47.
79. Hoang JV, Gadda G. Trapping choline oxidase in a nonfunctional conformation by freezing at low pH. Proteins 2007;66:611-20.
80. Finnegan S, Gadda G. Substitution of an active site valine uncovers a kinetically slow equilibrium between competent and incompetent forms of choline oxidase. Biochemistry 2008;47:13850-61.
81. Ghanem M, Gadda G. On the catalytic role of the conserved active site residue His466 of choline oxidase. Biochemistry 2005;44:893-904.
82. Heuts DP, Scrutton NS, McIntire WS, Fraaije MW. What's in a covalent bond? On the role and formation of covalently bound flavin cofactors. FEBS J 2009;276:3405-27.
83. Gadda G, Fan F, Hoang JV. On the contribution of the positively charged headgroup of choline to substrate binding and catalysis in the reaction catalyzed by choline oxidase. Arch Biochem Biophys 2006;451:182-7.
84. Gadda G, Powell NL, Menon P. The trimethylammonium headgroup of choline is a major determinant for substrate binding and specificity in choline oxidase. Arch Biochem Biophys 2004;430:264-73.
85. Fan F, Germann MW, Gadda G. Mechanistic studies of choline oxidase with betaine aldehyde and its isosteric analogue 3,3-dimethylbutyraldehyde. Biochemistry 2006;45:1979-86.
86. Gadda G. pH and deuterium kinetic isotope effects studies on the oxidation of choline to betaine-aldehyde catalyzed by choline oxidase. Biochim Biophys Acta 2003;1650:4-9.
87. Quaye O, Cowins S, Gadda G. Contribution of flavin covalent linkage with histidine 99 to the reaction catalyzed by choline oxidase. J Biol Chem 2009;284:16990-7.
88. Rungsrisuriyachai K, Gadda G. On the role of histidine 351 in the reaction of alcohol oxidation catalyzed by choline oxidase. Biochemistry 2008;47:6762-9.
89. Rungsrisuriyachai K, Gadda G. Role of asparagine 510 in the relative timing of substrate bond cleavages in the reaction catalyzed by choline oxidase. Biochemistry 2010;49:2483-90.
90. Fan F, Gadda G. An internal equilibrium preorganizes the enzyme-substrate complex for hydride tunneling in choline oxidase. Biochemistry 2007;46:6402-8.
91. Fan F, Gadda G. Oxygen- and temperature-dependent kinetic isotope effects in choline oxidase: correlating reversible hydride transfer with environmentally enhanced tunneling. J Am Chem Soc 2005;127:17954-61.
92. Quaye O, Gadda G. Effect of a conservative mutation of an active site residue involved in substrate binding on the hydride tunneling reaction catalyzed by choline oxidase. Arch Biochem Biophys 2009;489:10-4.
93. Yuan H, Gadda G. Importance of a serine proximal to the C(4a) and N(5) flavin atoms for hydride transfer in choline oxidase. Biochemistry 2011;50:770-9.
94. Quaye O, Nguyen T, Gannavaram S, Pennati A, Gadda G. Rescuing of the hydride transfer reaction in the Glu312Asp variant of choline oxidase by a substrate analogue. Arch Biochem Biophys 2010;499:1-5.
95. Hernandez-Ortega A, Borrelli K, Ferreira P, Medina M, Martinez AT, Guallar V. Substrate diffusion and oxidation in GMC oxidoreductases: an experimental and computational study on fungal aryl-alcohol oxidase. Biochem J 2011;436:341-50.
96. Wongnate T, Sucharitakul J, Chaiyen P. Identification of a catalytic base for sugar oxidation in the pyranose 2-oxidase reaction. Chembiochem 2011;12:2577-86.
97. Canovas D, Vargas C, Kneip S, et al. Genes for the synthesis of the osmoprotectant glycine betaine from choline in the moderately halophilic bacterium Halomonas elongata DSM 3043, USA. Microbiology 2000;146 ( Pt 2):455-63.
98. Yilmaz JL, Bulow L. Enhanced stress tolerance in Escherichia coli and Nicotiana tabacum expressing a betaine aldehyde dehydrogenase/choline dehydrogenase fusion protein. Biotechnol Prog 2002;18:1176-82.
99. Rendina G, Singer TP. Solubilization and assay of choline dehydrogenase. Biochim Biophys Acta 1958;30:441-2.
100. Gomez-Moreno C, Choy M, Edmondson DE. Purification and properties of the bacterial flavoprotein: thiamin dehydrogenase. J Biol Chem 1979;254:7630-5.
101. Kenney WC, Edmondson DE, Seng RL. Identification of the covalently bound flavin of thiamin dehydrogenase. J Biol Chem 1976;251:5386-90.
102. Gomez-Moreno C, Edmondson DE. Evidence for an aldehyde intermediate in the catalytic mechanism of thiamine oxidase. Arch Biochem Biophys 1985;239:46-52.
103. Kenney WC, Edmondson DE, Singer TP. A novel form of covalently bound flavin from thiamine dehydrogenase. Biochem Biophys Res Commun 1974;57:106-11.
104. Edmondson DE, Kenney WC. Identification and properties of 8alpha-(N(1)-histidyl)-riboflavin: the flavin component of thiamine dehydrogenase and beta-cyclopiazonate oxidocyclase. Biochem Biophys Res Commun 1976;68:242-8.