High-yielding cascade enzymatic synthesis of 5-methyluridine using a novel combination of nucleoside phosphorylases

References

• Brady D, Steenkamp L, Skein E, Chaplin JA, Reddy S. 2004. Optimisation of the enantioselective biocatalytic hydrolysis of naproxen ethyl ester using ChiroCLEC-CR. Enzyme Microb Technol 34:283–291.
   Web of Science ®Google Scholar
• Bzowska A, Kulikowska E, Shugar D. 2000. Purine nucleoside phosphorylases: properties, functions, and clinical aspects. Pharmacol Ther 88:349–425.
   PubMed Web of Science ®Google Scholar
• Cacciapuoti G, Forte S, Moretti MA Brio A, Zappia V, Porcelli M. 2005. A novel hyperthermostable 5′-deoxy-5′-methylthioadenosine phosphorylase from the archaeon Sulfolobus solfataricus. FEBS J 272:1886–1899.
   Google Scholar
• Cacciapuoti G, Gorassini S, Mazzeo MF, Siciliano RA, Carbone V, Zappia V, Porcelli M. 2007. Biochemical and structural characterization of mammalian-like purine nucleoside phosphorylase from the archaeon Pyrococcus furiosus. FEBS J 274:2482–2495.
   Google Scholar
• Chen B-C, Quinlan SL, Gregory Reid J. 1995. A new synthesis of the anti-AIDS drug AZT from 5-methyluridine. Tetrahedron Lett 36:7961–7964.
   Google Scholar
• Dandanell G, Szczepanowski RH, Kierdaszuk B. Shugar D. Bochtler M. 2005. Escherichia coli purine nucleoside phosphorylase II, the product of the xapA gene. J Mol Biol 348:113–125.
   Google Scholar
• Erion MD, Takabayashi K, Smith HB, Kessi J, Wagner S, Hönger S, Shames SL, Ealick SE. 1997. Purine nucleoside phosphorylase. 1. Structure–function studies. Biochemistry 36:11725–11734.
   PubMedGoogle Scholar
• Fox JJ, Yung N, Davoll J, Brown GB. 1956. Pyrimidine nucleosides. I. A new route for the synthesis of thymine nucleosides. J Am Chem Soc 78:2117–2122.
   Web of Science ®Google Scholar
• Freskos JN, Senaratne K, Pushpananda A. 1990. Synthesis of beta-thymidine. US patent 4, 914, 233.
   Google Scholar
• Hammer-Jespersen K, Munch-Petersen A, Schwartz M, Nygaard P. 1971. Induction of enzymes involved in the catabolism of deoxyribonucleosides and ribonucleosides in Escherichia coli K 12. Eur J Biochem 19:533–538.
   Google Scholar
• Hanrahan JR, Hutchinson DW. 1992. The enzymatic-synthesis of antiviral agents. J Biotechnol 23:193–210.
   PubMed Web of Science ®Google Scholar
• Hori N, Watanabe M, Yamazaki Y, Mikami Y. 1989a. Synthesis of 5-methyluridine by a thermophile, Bacillus stearothermophilus JTS 859. Agric Biol Chem 53:197–202.
   Web of Science ®Google Scholar
• Hori N, Watanabe M, Yamazaki Y, Mikami Y. 1989b. Purification and characterization of thermostable purine nucleoside phosphorylase from Bacillus stearothermophilus JTS 859. Agric Biol Chem 53:2205–2210.
   Web of Science ®Google Scholar
• Hori N, Watanabe M, Sunagawa K, Uehara K, Mikami Y. 1991a. Production of 59′-methyluridine by immobilized thermostable purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase from Bacillus stearothermophilus JTS 859. J Biotechnol 17:121–131.
   PubMed Web of Science ®Google Scholar
• Hori N, Watanabe M, Mikami Y. 1991b. The effects of organic solvent on the ribosyl transfer reaction by thermostable purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase from Bacillus stearothermophilus JTS 859. Biocatal Biotransform 4:297–304.
   Google Scholar
• Hwang WI, Cha S. 1973. A new enzymatic method for the determination of inorganic phosphate and its application to the nucleoside diphosphatase assay. Anal Biochem 55:379–387.
   PubMed Web of Science ®Google Scholar
• Ishii M, Shirae H, Yokozeki K. 1989. Enzymatic production of 5-methyluridine from purine nucleosides and thymine by Erwinia cartovora AJ-2992. Agric Biol Chem 53:3209–3218.
   Web of Science ®Google Scholar
• Lee J, Filosa S, Bonvin J, Guyon S, Aponte R, Turnbull J. 2001. Expression, purification, and characterization of recombinant purine nucleoside phosphorylase from Escherichia coli. Protein Expr Purif 22:180–188.
   PubMed Web of Science ®Google Scholar
• Lewkowicz ES, Iribarren AM. 2006. Nucleoside phosphorylases. Curr Org Chem 10:1197–1215.
   Web of Science ®Google Scholar
• Louw ME, Reid SJ, Watson TG. 1993. Characterization, cloning and sequencing of a thermostable endo-(1,3-1,4) β-glucanase-encoding gene from an alkalophilic Bacillus brevis. Appl Microbiol Biotechnol 38:507–513.
   PubMedGoogle Scholar
• Mikhailopulo IA. 2007. Biotechnology of nucleic acid constituents – state of the art and perspectives. Curr Org Chem 11:317–335.
   Web of Science ®Google Scholar
• Prasad AK, Trikha S, Parmar VS. 1999. Nucleoside synthesis mediated by glycosyl transferring enzymes. Bioorg Chem 27:135–154.
   Web of Science ®Google Scholar
• Sambrook J, Russell DW. 2001. Molecular cloning: A laboratory manual. Cold Spring Harbor (NY): Cold Spring Harbor Press.
   Google Scholar
• Shiragami H, Ineyama T, Uchida Y, Izawa K. 1996. Synthesis of 1-(2,3-dideoxy-β-d-glycero-pent-2-enofuranosyl)thymine (d4t; stavudine) from 5-methyluridine. Nucleosides Nucleotides Nucleic Acids 15:47–58.
   Web of Science ®Google Scholar
• Spoldi E, Ghisotti D, Cali S, Grisa M, Orsini G, Tonon G, Zuffi G. 2001. Recombinant bacterial cells as efficient biocatalysts for the production of nucleosides. Nucleosides Nucleotides Nucleic Acids 20:977–979.
   PubMed Web of Science ®Google Scholar
• Steenkamp L, Brady D. 2008. Optimisation of stabilised carboxylesterase NP for enantioselective hydrolysis of naproxen methyl ester. Process Biochem 43:1419–1426.
   Google Scholar
• Stepanenko BN, Kaz'mina EM, Dubinkina ZS. 1973. Methods of synthesis of pyrimidine nucleosides. Russ Chem Rev 42:494–508.
   Google Scholar
• Tonon G, Capra E, Orsini G, Zuffi G. 2004. Novel immobilized biocatalysts usable for the production of natural nucleosides and modified analogs by enzymatic transglycosylation reactions. US Patent Application 20040142438.
   Google Scholar
• Utagawa T. 1999. Enzymatic preparation of nucleoside antibiotics. J Mol Catal B: Enzym 6:215–222.
   Web of Science ®Google Scholar
• Visser DF, Gordon G, Bode ML, Hennessy F, Rashamuse K, Louw ME, Brady D. 2009. A biocatalytic method for synthesis of 5-methyluridine. Patent number:WO2010055369.
   Google Scholar
• Visser DF, Hennessy F, Rashamuse K, Louw M, Brady D. 2010. Cloning, purification and characterisation of a recombinant purine nucleoside phosphorylase from Bacillus halodurans Alk36. Extremophiles 14:185–192.
   Google Scholar