Biotransformation of 2,6-diaminopurine nucleosides by immobilized Geobacillus stearothermophilus

Biotechnology Progress

Volumn 28, Issue 5, 2012, Pages 1251-1256

  De Benedetti, Eliana C ^a   Rivero, Cintia W ^a   Britos, Claudia N ^a   Lozano, Mario E ^a   Trelles, Jorge A ^a  

^a UNIVERSIDAD NACIONAL DE QUILMES   (Argentina)

Author keywords

Nucleoside phosphorylase; Prodrug precursors; Thermophilic microorganisms; Transglycosylation; Whole cell immobilization

Indexed keywords

AGAROSE; ANTISENSE OLIGONUCLEOTIDES; BIOPROCESSES; CONVERSION RATES; GEOBACILLUS STEAROTHERMOPHILUS; NUCLEOSIDE ANALOGUES; NUCLEOSIDE PHOSPHORYLASE; PRODRUGS; THERMOPHILIC BACTERIA; THERMOPHILIC MICROORGANISMS; TRANSGLYCOSYLATION;

CELL IMMOBILIZATION; PHOSPHORYLATION;

BIOMOLECULES;

2 AMINOPURINE; 2,6 DIAMINOPURINE; 2,6-DIAMINOPURINE; DRUG DERIVATIVE; NUCLEOSIDE;

ARTICLE; BIOTRANSFORMATION; GEOBACILLUS STEAROTHERMOPHILUS; IMMOBILIZED CELL; METABOLISM;

2-AMINOPURINE; BIOTRANSFORMATION; CELLS, IMMOBILIZED; GEOBACILLUS STEAROTHERMOPHILUS; NUCLEOSIDES;

BACTERIA (MICROORGANISMS); GEOBACILLUS STEAROTHERMOPHILUS;

EID: 84867399630     PISSN: 87567938     EISSN: 15206033     Source Type: Journal    
DOI: 10.1002/btpr.1602     Document Type: Article

References (28)

1. Mikhailopulo IA, Miroshnikov AI. Biologically important nucleosides: modern trends in biotechnology and application. Mendeleev Commun. 2011; 21: 57-68.
2. Okuyama K, Susumu S, Hamamoto T, Noguchi T. Enzymatic synthesis of 2′-deoxyguanosine with nucleoside deoxyribosyltransferase-II. Biosci Biotech Biochem. 2003; 67: 989-995.
3. Rosenbohm C, Pedersen DS, Frieden M, Jensen FR, Arent S, Larsen S, Koch T. LNA guanine and 2, 6-diaminopurine. Synthesis, characterization and hybridization properties of LNA 2, 6-diaminopurine containing oligonucleotides. Bioorg Med Chem. 2004; 12: 2385-2396.
4. Kore A, Charles I. Synthesis of new dinucleotide mRNA cap analogs containing 2, 6-diaminopurine moiety. Lett Org Chem 2010; 7: 200-202.
5. Arico JW, Calhoun AK, McLaughlin LW. Preparation of the 2′-deoxynucleosides of 2, 6-diaminopurine and isoguanine by direct glycosylation. J Org Chem. 2010; 75: 1360-1365.
6. Li N, Smith TJ, Zong M-H. Biocatalytic transformation of nucleoside derivatives. Biotechnol Adv. 2010; 28: 348-366.
7. Trelles JA, Valino AL, Runza V, Lewkowicz ES, Iribarren AM. Screening of catalytically active microorganisms for the synthesis of 6-modified purine nucleosides. Biotechnol Lett. 2005; 27: 759-763.
8. Tao J, Xu J-H. Biocatalysis in development of green pharmaceutical processes. Curr Opin Chem Biol. 2009; 13: 43-50.
9. Almendros M, Berenguer J, Sinisterra JV. Thermus thermophilus nucleoside phosphorylases active in the synthesis of nucleoside analogues. Appl Environ Microbiol. 2012; 78: 3128-3135.
10. Fernández-Lucas J, Acebal C, Sinisterra JV, Arroyo M, de la Mata I. Lactobacillus reuteri 2′-deoxyribosyltransferase, a novel biocatalyst for tailoring of nucleosides. Appl Environ Microb. 2010; 76: 1462-1470.
11. Ishige T, Honda K, Shimizu S. Whole organism biocatalysis. Curr Opin Chem Biol. 2005; 9: 174-180.
12. Yokozeki K, Tsuji T. A novel enzymatic method for the production of purine-2′-deoxyribonucleosides. J Mol Catal B: Enzym. 2000; 10: 207-213.
13. Demirjian DC, Morís-Varas F, Cassidy CS. Enzymes from extremophiles. Curr Opin Chem Biol. 2001; 5: 144-151.
14. Bzowska A, Kulikowska E, Shugar D. Purine nucleoside phosphorylases: properties, functions, and clinical aspects. Pharmacol Ther. 2000; 88: 349-425.
15. Guisán JM. Immobilization of enzymes and cells. Methods Biotechnol. 2006: 347-356.
16. Trelles JA, Fernández-Lucas J, Condezo LA, Sinisterra JV. Nucleoside synthesis by immobilised bacterial whole cells. J Mol Catal B: Enzym. 2004; 30: 219-227.
17. Kamat SS, Bagaria A, Kumaran D, Holmes-Hampton GP, Fan H, Sali A, Sauder J M, Burley SK, Lindahl PA, Swaminathan S, Raushel FM. Catalytic mechanism and three-dimensional structure of adenine deaminase. Biochemistry. 2011; 50: 1917-1927.
18. Rivero CW, Britos CN, Lozano ME, Sinisterra JV, Trelles JA. Green biosynthesis of floxuridine by immobilized microorganisms. FEMS Microbiol Lett. 2012; 331: 31-36.
19. Hamamoto T, Noguchi T, Midorikawa Y. Purification and characterization of purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase from Bacillus stearothermophilus TH 6-2. Biosci Biotech Biochem. 1996; 60: 1179-1180.
20. Utagawa T. Enzymatic preparation of nucleoside antibiotics. J Mol Catal B: Enzym. 1999; 6: 215-222.
21. Janulczyk R, Pallon J, Björck L. Identification and characterization of a Streptococcus pyogenes ABC transporter with multiple specificity for metal cations. Mol Microbiol. 1999; 34: 596-606.
22. Martinussen J, Sørensen C, Jendresen CB, Kilstrup M. Two nucleoside transporters in Lactococcus lactis with different substrate specificities. Microbiology. 2010; 156: 3148-3157.
23. Vahedi-Faridi A, Eckey V, Scheffel F, Alings C, Landmesser H, Schneider E, Saenger W. Crystal structures and mutational analysis of the arginine-, lysine-, histidine-binding protein ArtJ from Geobacillus stearothermophilus. Implications for interactions of ArtJ with its cognate ATP-binding cassette transporter, Art(MP)2. J Mol Biol. 2008; 375: 448-459.
24. Britos CN, Cappa VA, Rivero CW, Sambeth JE, Lozano ME, Trelles JA. Biotransformation of halogenated 2′-deoxyribosides by immobilized lactic acid bacteria. J Mol Catal B: Enzym. 2012; 79: 49-53.
25. Ansorge-Schumacher MB, Slusarczyk H, Schümers J, Hirtz D. Directed evolution of formate dehydrogenase from Candida boidinii for improved stability during entrapment in polyacrylamide. FEBS J. 2006; 273: 3938-3945.
26. Tischer W, Kasche V. Immobilized enzymes: crystals or carriers? Trends Biotechnol. 1999; 17: 326-335.
27. Manolov RJ, Kambourova MS, Emanuilova EI. Immobilization of Bacillus stearothermophilus cells by entrapment in various matrices. Process Biochem. 1995; 30: 141-144.
28. Sheldon RA. E factors, green chemistry and catalysis: an odyssey. Chem Commun. 2008; 29: 3352-3365.