Stabilization of thymidine phosphorylase from Escherichia coli by immobilization and post immobilization techniques

Enzyme and Microbial Technology

Volumn 49, Issue 1, 2011, Pages 52-58

  Serra, Immacolata ^a   Serra, Carla Daniela ^b,c   Rocchietti, Silvia ^b   Ubiali, Daniela ^a   Terreni, Marco ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b Innovate Biotechnology srl   (Italy)

^c UNIVERSITY OF MILAN   (Italy)

Author keywords

5 fluoro 2 deoxyuridine; E. coli thymidine phosphorylase; Enzyme immobilization; Transglycosylation

Indexed keywords

5-FLUOROURACIL; ACTIVE CATALYST; AGAROSE; ALDEHYDE-DEXTRAN; COVALENT IMMOBILIZATION; DEOXYURIDINE; E. COLI; HIGH ACTIVITY; IMMOBILIZATION TECHNIQUE; IMMOBILIZED ENZYME; IONIC ADSORPTION; NO RELEASE; ONE-POT SYNTHESIS; OXIDATION DEGREE; POLYETHYLENEIMINE; SEPABEADS; SOLID SUPPORTS; THYMIDINE PHOSPHORYLASE; TRANSGLYCOSYLATION;

ADSORPTION; ALDEHYDES; DEXTRAN; ENZYME ACTIVITY; ESCHERICHIA COLI; GLUCOSE; ORGANIC COMPOUNDS; PHOSPHORYLATION; SYNTHESIS (CHEMICAL);

ENZYME IMMOBILIZATION;

BACTERIAL ENZYME; DEOXYURIDINE; FLOXURIDINE; FLUOROURACIL; THYMIDINE; THYMIDINE PHOSPHORYLASE;

ARTICLE; CATALYST; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME IMMOBILIZATION; ESCHERICHIA COLI; GLYCOSYLATION; NONHUMAN; PH; SYNTHESIS;

ADSORPTION; CATALYSIS; CROSS-LINKING REAGENTS; ENZYME STABILITY; ENZYMES, IMMOBILIZED; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; FLOXURIDINE; INDUSTRIAL MICROBIOLOGY; MICROSPHERES; SEPHAROSE; THYMIDINE PHOSPHORYLASE;

ESCHERICHIA COLI;

EID: 79957565591     PISSN: 01410229     EISSN: 18790909     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2011.03.011     Document Type: Article

References (58)

1. Levene P.A., Yamagawa M., Weber I. On nucleosidases. I. General properties. J Biol Chem 1924, 60:693-706.
2. Pugmire M.J., Ealich S.E. Structural analyses reveal two distinct families of nucleoside phosphorylases. Biochem J 2002, 361:1-25.
3. Krenitsky T.A. Pentosyl transfer mechanism of the mammalian nucleoside phosphorylases. J Biol Chem 1968, 243:2871-2875.
4. Prasad A.K., Trikha S., Parmar V.S. Nucleoside synthesis mediated by glycosyl transferring enzymes. Bioorg Chem 1999, 27:135-154.
5. Lewkowicz E.S., Iribarren A.M. Nucleoside phosphorylases. Curr Org Chem 2006, 10:1197-1215.
6. Mikhailopulo I.A. Biotechnology of nucleic acid constituents. State of art and perspectives. Curr Org Chem 2007, 11:317-335.
7. Bavaro T., Rocchietti S., Ubiali D., Filice M., Terreni M., Pregnolato M. A versatile synthesis of 5-functionalized nucleosides through regioselective enzymatic hydrolysis of their peracetylated precursors. Eur J Org Chem 2009, 12:1967-1975.
8. Burton S.G., Cowan D.A., Woodley J.M. The search for the ideal biocatalyst. Nature Biotech 2002, 20:37-45.
9. Polizzi K.M., Bommarius A.S., Broering J.M., Chaparro-Riggers J.F. Stability of biocatalysts. Curr Opin Chem Biol 2007, 11:220-225.
10. Cao L. Immobilised enzymes: science or art?. Curr Opin Chem Biol 2005, 9:217-226.
11. Mateo C., Palomo J.M., Fernandez-Lorente G., Guisan J.M., Roberto Fernandez-Lafuente Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb Technol 2007, 40:1451-1463.
12. Fernàndez-Lafuente R. Stabilization of multimeric enzymes: strategies to prevent subunit dissociation. Enzyme Microb Technol 2009, 45:405-418.
13. Abian O., Grazù V., Hermoso J., Gonzàlez R., García J.L., Fernàndez-Lafuente R., et al. Stabilization of penicillin G acylase from Escherichia coli: site-directed mutagenesis of the protein surface to increase multipoint covalent attachment. Appl Environ Microbiol 2004, 70:1249-1251.
14. Levene P.A., Medigreceanu F. On nucleases. J Biol Chem 1911, 9:65-83.
15. Panova N.G., Alexeev C.S., Kuzmichov A.S., Shcheveleva E.V., Gavryushov S.A., Polyakov K.M., et al. Substrate specificity of Escherichia coli thymidine phosphorylase. Biochemistry (Moscow) 2007, 72:21-28.
16. Hatano A., Harano A., Kirihara M. Importance of 3'-hydroxyl group of the nucleosides for the reactivity of thymidine phosphorylase from Escherichia coli. Chem Lett 2006, 35:232-233.
17. Panova N.G., Alexeev C.S., Polyakov K.M., Gavryushov S.A., Kritzyn A.M., Mikhailov S.N. Substrate specificity of thymidine phosphorylase of E. coli: role of hydroxyl groups. Nucleos, Nucleot Nucleic Acids 2008, 27:1211-1214.
18. Cook W.J., Koszalka G.W., Hall W.W., Burns C.L., Ealick S.E. Crystallization and preliminary X-ray investigation of thymidine phosphorylase from Escherichia coli. J Biol Chem 1987, 262:3788-3789.
19. Walter M.R., Cook W.J., Cole L.B., Short S.A., Koszalka G.W., Krenitsky T.A., et al. Three-dimensional structure of thymidine phosphorylase from Escherichia coli at 2.8Å resolution. J Biol Chem 1990, 265:14016-14022.
20. Moghaddam A., Bicknell R. Expression of platelet-derived endothelial cell growth factor in Escherichia coli and confirmation of its phosphorylase activity. Biochemistry 1992, 31:12141-12146.
21. Balzarini J., Degrève B., Esteban-Gamboa A., Esnouf R., De Clerc E., Engelborghs Y., et al. Kinetic analysis of novel multisubstrate analogue inhibitors of thymidine phosphorylase. FEBS Lett 2000, 483:181-185.
22. McNally V.A., Gbaj A., Douglas K.T., Stratford I.J., Jaffar M., Freemanan S., et al. Identification of a novel class of inhibitor of human and Escherichia coli thymidine phosphorylase by in silico screening. Bioorg Med Chem Lett 2003, 13:3705-3709.
23. Barai V.N., Zinchenko A.I., Eroshevskaya L.A., Kalinichenko E.N., Kulak T.I., Mikhailopulo I.A. A universal biocatalyst for the preparation of base- and sugar-modified nucleosides via an enzymatic transglycosylation. Helv Chim Acta 2002, 85:1901-1908.
24. D.F. Visser, G.E.R. Gordon, F. Hennessy, K.J. Rashamuse, D. Brady, M.L. Bode, et al., Biocatalytic preparation of nucleosides, WO 2010/055369 A1.
25. Krenitsky T.A., Koszalka G.W., Tuttle J.V. Purine nucleoside synthesis, an efficient method employing nucleoside phosphorylases. Biochemistry 1981, 20:3615-3621.
26. C.L. Burns, G.W. Koszalka, T.A. Krenitsky, Therapeutic nucleosides, WO 93/14103.
27. Roivainen J., Elizarova T., Lapinjoki S., Mikhailopulo I.A., Esipov R.S., Miroshnikov A.I. An enzymatic transglycosylation of purine bases. Nucleos Nucleot Nucleic Acids 2007, 26:905-909.
28. Rocchietti S., Ubiali D., Terreni M., Albertini A.M., Fernandez-Lafuente R., Guisan J.M., et al. Immobilization and stabilization of recombinant multimeric uridine and purine nucleoside phosphorylases from Bacillus subtilis. Biomacromolecules 2004, 5:2195-2200.
29. Hori N., Watanabe M., Sunagawa K., Uehara K., Mikami Y. Production of 5-methyluridine by immobilized thermostable purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase from Bacillus stearothermophilus JTS 859. J Biotechnol 1991, 17:121-131.
30. Zuffi G., Ghisotti D., Oliva I., Capra E., Frascotti G., Tonon G., et al. Immobilized biocatalysts for the production of nucleosides and nucleoside analogues by enzymatic transglycosylation reactions. Biocatal Biotransform 2004, 22:25-33.
31. Rick S.W., Abashkin Y.G., Hilderbrandt R.L., Burt S.K. Computational studies of the domain movement and the catalytic mechanism of thymidine phosphorylase. Proteins 1999, 37:242-252.
32. Avraham Y., Grossowic N., Yashphe J. Purification and characterization of uridine and thymidine phosphorylase from Lactobacillus casei. Biochim Biophys Acta 1990, 1040:287-293.
33. Desgranges C., Razaka G., Rabaud M., Bricaud H. Catabolism of thymidine in human blood platelets. Purification and properties of thymidine phosphorylase. Biochim Biophys Acta 1981, 654:211-218.
34. Pugmire M.J., Cook W.J., Jasanoff A., Walter M.R., Ealick S.E. Structural and theoretical studies suggest domain movement produces an active conformation of thymidine phosphorylase. J Mol Biol 1998, 281:285-299.
35. Fernandez-Lafuente R., Rodri{dotless}guez V., Mateo C., Penzol G., Hernandez-Justiz O., Irazoqui G., et al. Stabilization of multimeric enzymes via immobilization and post-immobilization techniques. J Mol Catal B 1999, 7:181-189.
36. Bolivar J.M., Rocha-Martin J., Mateo C., Cava F., Berenguer J., Fernandez-Lafuente R., et al. Coating of soluble and immobilized enzymes with ionic polymers: full stabilization of the quaternary structure of multimeric enzymes. Biomacromolecules 2009, 10:742-747.
37. Mateo C., Palomo J.M., Fuentes M., Betancor L., Grazu V., Lopez-Gallego F., et al. Glyoxyl agarose: a fully inert and hydrophilic support for immobilization and high stabilization of proteins. Enzyme Microb Technol 2006, 39:274-280.
38. Ubiali D., Rocchietti S., Scaramozzino F., Terreni M., Albertini A.M., Fernández-Lafuente R., et al. Synthesis of 2'-deoxynucleosides by transglycosylation with new immobilized and stabilized uridine phosphorylase and purine nucleoside phosphorylase. Adv Synth Catal 2004, 346:1361-1366.
39. Mateo C., Abian O., Fernandez-Lafuente R., Guisan J.M. Increase in conformational stability of enzymes immobilized on epoxy-activated supports by favoring additional multipoint covalent attachment. Enzyme Microb Technol 2000, 26:509-515.
40. Katchalski-Katzir E., Kraemer D.M. Eupergit C, a carrier for immobilization of enzymes of industrial potential. J Mol Catal B 2000, 10:157-176.
41. Bolivar J.M., Cava F., Mateo C., Rocha-Martín J., Guisán J.M., Berenguer J., et al. Immobilization-stabilization of a new recombinant glutamate dehydrogenase from Thermus thermophiles. Appl Microbiol Biotechnol 2008, 80:49-58.
42. Bolivar J.M., Wilson L., Ferrarotti S.A., Fernandez-Lafuente R., Guisan J.M., Mateo C. Stabilization of a formate dehydrogenase by covalent immobilization on highly activated glyoxyl agarose supports. Biomacromolecules 2006, 7:669-673.
43. Mateo C., Abian O., Fernandez-Lorente G., Pedroche J., Fernandez-Lafuente R., Guisan J.M., et al. Epoxy Sepabeads®: a novel epoxy support for stabilization of industrial enzymes via very intense multipoint covalent attachment. Biotechnol Prog 2002, 18:629-634.
44. Boller T., Meier C., Menzler S. EUPERGIT oxirane acrylic beads: how to make enzymes fit for biocatalysis. Org Process Res Dev 2002, 6:509-519.
45. Temporini C., Bonomi P., Serra I., Tagliani A., Bavaro T., Ubiali D., et al. Characterization and study of the orientation of immobilized enzymes by tryptic digestion and HPLC-MS: design of an efficient catalyst for the synthesis of cephalosporins. Biomacromolecules 2010, 11:1623-1632.
46. Okuyama K., Shibuya S., Hamamoto T., Noguchi T. Enzymatic synthesis of 2'-deoxyguanosine with nucleoside deoxyribosyltransferase-II. Biosci Biotechnol Biochem 2003, 67:989-995.
47. Komatsu H., Awano H., Ishibashi H., Ikeda I. Development of chemo-enzymatic process and manufacture of deoxynucleosides. Nucleic Acids Res 2001, (Suppl. 1):49-50.
48. Fernandez-Lafuente R., Rosell C.M., Rodriguez V., Santana C., Soler G., Bastida A., et al. Preparation of activated supports containing low pK amino groups. A new tool for protein immobilization via the carboxyl coupling method. Enzyme Microb Technol 1993, 15:546-550.
49. Guisàn J.M. Aldehyde-agarose gels as activated supports for immobilization-stabilization of enzymes. Enzyme Microb Technol 1988, 10:375-382.
50. Drobchenko S.V., Isaeva-Ivanova L.S., Kleiner A.R., Lomakin A.V., Kolker A.R., Noskin V.A. An investigation of the structure of periodate oxidised dextran. Carbohyd Res 1993, 241:189-199.
51. Guisàn J.M., Bastida A., Blanco R.M., Fernandez-Lafuente R., Garcia-Junceda E. Immobilization of enzymes on glyoxyl agarose. Immobilization of enzymes and cells 1997, 277-287. Humana Press Inc., Totowa, NJ. G.F. Bickerstaff (Ed.).
52. Mateo C., Fernandez-Lorente G., Abian O., Fernandez-Lafuente R., Guisan J.M. Multifunctional epoxy supports: a new tool to improve the covalent immobilization of proteins. The promotion of physical adsorptions of proteins on the supports before their covalent linkage. Biomacromolecules 2000, 1:739-745.
53. Bradford M.M. A rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principle of protein-dye-binding. Anal Biochem 1976, 72:248-254.
54. Terreni M., Ubiali D., Bavaro T., Cecchini D.A., Serra I., Pregnolato M. Bioprocesses for the synthesis of nucleosides and nucleotides. Biocatalysis research progress 2008, 47-94. Nova Science Publishers Inc., New York. F.H. Romano, A. Russo (Eds.).
55. López-Gallego F., Betancor L., Mateo C., Hidalgo A., Alonso-Morales N., Dellamora-Ortiz G., et al. Enzyme stabilization by glutaraldehyde crosslinking of adsorbed proteins on aminated supports. J Biotechnol 2005, 119:70-75.
56. Poltorak O.M., Chkhray E.S., Torshin I.Y. Dissociative thermal inactivation, stability, and activity of oligomeric enzymes. Biochemistry 1998, 63:303-311.
57. Krenitsky T.A, Tuttle J.V. Correlation of substrate-stabilization patterns with proposed mechanisms for three nucleoside phosphorylases. Biochim Biophys Acta 1982, 703:247-249.
58. Mateo C., Abian O., Fernandez-Lafuente R., Guisàn J.M. Reversible enzyme immobilization via a very strong and non distorting ionic adsorption on support-polyethylenimine composites. Biotechnol Bioeng 2000, 68:98-105.