Biotechnologia Acta


  • Increase font size
  • Default font size
  • Decrease font size
Print PDF

ISSN 2410-7751 (Print)
ISSN 2410-776X (Online)

Biotechnologia Acta
V. 6, No 4, 2013

"Biotechnologia Acta" v. 6, no. 4, 2013
doi: 10.15407/biotech6.04.063
Р. 63-77, Bibliography 34, English
Universal Decimal classification: 577.113.3


A. Mikhailopulo1, A. I. Miroshnikov2

1Institute of Bioorganic Chemistry of Belarus National Academy of Sciences, Minsk, Belarus
2Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry of Russian Academy of Sciences, Moscow, Russia

Some recent findings in the biotechnology of biologically important nucleosides will be discussed, viz., (i) a new strategy of the cascade one-pot transformation of D-pentoses into nucleosides based on the extension and deepening of the knowledge of the mechanism of functioning of the ribokinase, phosphopentomutase, and uridine, thymidine and purine nucleoside (PNP) phosphorylases, and the role of different factors (structural, electronic, stereochemical) in the glycoside bond formation, (ii) the modern chemistries of the chemo-enzymatic syntheses of nucleosides, (iii) the transglycosylation reaction using natural and sugar modified nucleosides as donors of carbohydrate residues and heterocyclic bases as acceptors catalyzed by nucleoside phosphorylases (NP).

Key words: nucleosides, bio-mimetic synthesis, chemo-enzymatic synthesis, enzymes of nucleic acid metabolism.

© Palladin Institute of Biochemistry of National Academy of Sciences of Ukraine, 2008

  • References
    • 1. Mikhailopulo I. A. Biotechnology of Nucleic Acid Constituents — State of the Art and Perspectives. Current Org. Chem. 2007,  V. 11, P. 317.

      2. Mikhailopulo I. A.,Miroshnikov A. I. New Trends in Nucleoside Biotechnology. Acta Naturae. 2010, 2(5), 36.

      3. Mikhailopulo I. A., Miroshnikov A. I. Biologically important nucleosides: modern trends in biotechnology and application. Mendeleev Communs. 2011, V. 21, P. 57.

      4. Doskocil J., Holy A. Coll. Czech. Chem. Communs. 1977, V. 42, P. 370 (see also the works cited therein); Votruba I., Holy A., Dvorakova H. Mendeleev Communs. 1994, V. 59, P. 2303.

      5.Chuvikovsky D. V., Esipov R. S., Skoblov Y. S. Bioorg. Med. Chem. 2006. V. 14. P. 6327.

      6. Esipov R. S., Gurevich A. I., Chuvikovsky D. V. Protein Expes. Purif. 2002, V. 24, P. 56.

      7. Miroshnikov A. I., Esipov R. S., Konstantinova I. D. The Open Conference Proc. J2010, V. 1, P. 98.

      8. Stepchenko V. A., Seela F., Esipov R. S. Enzymatic Synthesis of 8-Azapurineand 8-Aza-7-deazapurine 2’-Deoxyribonucleosides. SynLett. 2012, V. 23, P. 1541.

      9. De Clercq E. Adv. Virus Res. 2009, V. 73, P. 1.

      10. Krosky P. M., Borysko K. Z., Nassiri M. R. Antimicrob. Agents Chemother. 2002, V. 46, P. 478; Evers D. L., Komazin G., Shin D. Antiviral Res. 2002, V. 56, P. 61; Gudmundsson K. S., Tidwell J., Lippa N. J. Med. Chem. 2000, V. 43, P. 2464.

      11. Prichard M. N. Rev. Med. Virol. 2009, V. 19, P. 215; Williams S. L., Hartline C. B., Kushner N. L. Antimicrob. Agents Chemother. 2003, V. 47, P. 2186; Hwang J. S., Kregler O., Schilf R. Virol. 2007, V. 81, P. 11604; Hwang J. S., Schilf R., Drach J. C. Antimicrob. Agents Chemother. 2009, V. 53, P. 5095.

      12. Trofe J., Pote L., Wade E.  Ann. Pharmacother. 2008, V. 42, P. 1447; Drugs R. D. Maribavir: 1263W94, Benzimidavir, GW 1263, GW 1263W94, VP41263. 2007, V. 8, P. 188; Chou S., Marousek G. I. J. Virol. 2008, V. 82, P. 246.

      13. Galmarini C. M., Popowycz F., Joseph B. Curr. Med. Chem. 2008, V. 15, P. 1072; Mathe C., Gosselin G. Antiviral Res. 2006, V. 71, P. 276; Biron K. K. Antiviral Res. 2006, V. 71. P. 154.

      14. Mikhailopulo I. A., Zinchenko A. I., Bokut S. B. Biotechnol. Letters. 1992, V. 14, P. 885.

      15. Mikhailopulo I. A., Kazimierczuk Z., Zinchenko A. I. Nucl. Acids Symp. Ser. 1994, N 31, P. 83.

      16. Mikhailopulo I. A., Kazimierczuk Z., Zinchenko A. I. Nucleosides Nucleotides. 1995, V. 14, P. 477.

      17. Bentancor L., Trelles J. A., Nóbile M. J. Mol. Cat. B: Enzymatic. 2004, V. 29, P. 3.

      18. Konstantinova I. D., Selezneva O. M., Fateev I. V. Synthesis. 2013, V. 45, P. 272.

      19. (a) MacDonald D. L. J. Org. Chem. 1962, V. 27, P. 1107;

      (b) MacDonald D. L. Carbohyd. Res. 1966, V. 3, P. 117;

      (c) MacDonald D. L. Carbohyd. Res. 1968, V. 6, P. 376; (c) Mendicino J., Hanna R. J. Biol. Chem. 1970. V. 245. P. 6113;

      (d) Chittenden G. J. F. Carbohyd. Res. 1972, V. 25. P. 35.

      20. Konstantinova I. D., Antonov K. V., Fateev I. V. Synthesis. 2011, V. 10, P. 1555.

      21. Wright R. S., Khorana H. G. J. Am. Chem. Soc. 1958, V. 80, P. 1994.

      22. Averett D. R., Koszalka G. W., Fyfe J. A. Antimicrob. Agents Chemother. 1991, V. 35, P. 851.

      23. Fateev I. V., Antonov K. V., Konstantinova I. D. The Chemo-Enzymatic Synthesis of Clofarabine and Related Nucleosides. The Role of Electronic and Stereochemical Factors of Substrates in Reactions Catalyzed by E. coli Nucleoside Phosphorylases. Federation of European Biochemical Societies. CONGRESS 2013 «Mechanisms in Biology», July 6–11, 2013. Sainct Petersburg, Russia. Abstracts.

      24. Roivainen J., Elizarova T., Lapinjoki S. Nucleosides, Nucleotides & Nucl. Acids. 2007, V. 26, P. 905.

      25. a) Himmerlsbach F., Shulz B. S., Trichtinger T. Tetrahedron. 1984, V. 40, P. 59;

      b) Zhou J., Tsai J.-Y., Bouhadir K., Slevin P. B.  Synthetic Commun. 1999, V. 29, P. 3003.

      26. Kulikovskiy A. I., Esipov R. S., Miroshnikov A. I., Mikhailopulo I. A. An Enzymatic Synthesis of Nucleosides of N2-Acetyl-O6-[2-(4-nitrophenyl)ethyl]guanine. Collection Symp. Series. 2011, V. 12, P. 397.

      27. Elion G. B. Cancer Res. 1969, V. 29, P. 2448.

      28. (a) Seela F., Pujari S. Bioconjugate Chem. 2010, V. 21, P. 1629;

      (b) Jiang D., Seela F. J. Am. Chem. Soc. 2010, V. 132, P. 4016.

      29. Seela F., Jiang D., Xu K. Org. Biomol. Chem. 2009, V. 7, P. 3463, and references cited therein.

      30. (a) Pokharel S., Jayalath P., Maydanovych O. J. Am. Chem. Soc. 2009, V. 131, P. 11882;

      (b) Veliz E. A., Easterwood L. M., Beal P. A. J. Am. Chem. Soc. 2003, V. 125, P. 10867;

      (c) Wier­zchows­ki J., Ogiela M., Iwanska B., Shugar D. Anal. Chim. Acta. 2002, V. 472, P. 63.

      31. (a) Elliot R. D., Montgomery J. A. J. Med. Chem. 1976. V. 19. P. 1186;

      (b) Kazimierczuk Z., Cottam H. B., Revankar G. R., Robins R. K. J. Am. Chem. Soc. 1984, V. 106, P. 6379, and references therein.

      32. (a) Doskocil J., Holy A. Coll. Czech. Chem. Communs. 1977, V. 42, P. 370 (see also the works cited therein);

      (b) Wierzchowski J., Wielgus-Kutrowska B., Shugar D. Biochim. Biophys. Acta. 1996. V. 1290, P. 9;

      (c) Votruba I., Holy A., Dvorakova H. Coll. Czech. Chem. Communs. 1994, V. 59, P. 2303.

      33. (a) Koellner G., Luic M., Shugar D. J. Mol. Biol. 1998, V. 280, P. 153;

      (b) Koellner G., Bzowska A., Wielgus-Kutrowska B. J. Mol. Biol. 2002, V. 315, P. 351;

      (c) Bennett E. M., Li C., Allan P. W. J. Biol. Chem. 2003, V. 278.  Mikleusevic G., Stefanic Z., Narczyk M. Biochimie. 2011, V. 93, P. 1610.

      34. Fateev I. V., Esipov R. S., Antonov K. V. The Role of the Ser90 Residue of the Catalytic Site of E. coli PNP in the Synthesis of Purine and 8-aza-7-deazapurine Nucleosides. Federation of European Biochemical Societies. CONGRESS 2013 «Mechanisms in Biology»; July 6–11, 2013.  Sainct Petersburg, Russia. Abstracts.