Skip to main content
SpringerLink
Log in

The arsenolysis reaction in the biotechnological method of synthesis of modified purine β-D-arabinonucleosides

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

We found a unique property of E. coli purine nucleoside phosphorylases to selectively perform the arsenolysis reaction of ribonucleosides in their active site without affecting β-D-arabinonucleosides. In the synthesis of modified β-D-arabinonucleosides from the corresponding ribonucleosides, the catalytical amount of sodium arsenate in the transglycosylation reaction provided a 95 to 98% conversion rate. Such an approach was shown to simplify the composition of the reaction mixtures and facilitate the isolation of the target nucleosides, particularly, vidarabine, fludarabine, and nelarabine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

Ara-A:

9-(β-D-arabinofuranosyl)adenine (vidarabin)

Ara-Basem :

arabinonucleoside modified at the purine base

Ara-U:

1-(β-D-arabinofuranosyl)uracil

D-Ara1αP :

1-α-D-phosphoro-D-arabinose

Bm :

modified purine base

F-Ade:

2-fluoroadenine

F-Ado:

2-fluoroadenosine

Flud:

2fluoro-9-(β-D-arabinofuranosyl)adenine (fludarabine)

6OMe-Gua:

6-O-methylguanine

6-OMe-Guo:

6-O-methylguanosine

Nel:

6-O-methyl-9-(β-D-arabinofuranosyl)guanine (nelarabine)

PNP:

purine nucleoside phosphorylase

RibBasem :

ribonucleoside modified at the purine base

UP:

uridine phosphorylase

Ura:

uracil

Urd:

uridine

NP:

nucleoside phosphorylase

References

  1. Lakshman, M.K., Modified Nucleosides in Biochemistry, Biotechnology and Medicine, Herdewijn, P., Ed., Wiley-VCH, 2008.

  2. Mikhailopulo, I.A. and Miroshnikov, A.I., Acta Naturae, 2010, vol. 2, pp. 38–61.

    Google Scholar 

  3. De Clercq, Annu. Rev. Pharmacol. Toxicol., 2011, vol. 51, pp. 1–24.

    Article  CAS  PubMed  Google Scholar 

  4. Bzowska, A., Kulikowska, E., and Shugar, D., Pharmacol. Therap., 2000, vol. 88, pp. 349–425.

    Article  CAS  Google Scholar 

  5. Konstantinova, I.D., Antonov, K.V., Berzin, V.B., Dorofeeva, E.V., Fateev, I.V., Muzyka, I.S., and Miroshnikov, A.I., RF Patent No. 2368662, 2009.

    Google Scholar 

  6. Bokut’, S.B., Barai, V.N., and Zinchenko, A.I., Prikl. Biokhim. Mikrobiol., 1995, vol. 31, no. 3, pp. 308–310.

    PubMed  Google Scholar 

  7. Kline, P.C. and Schramm, V.L., Biochemistry, 1993, vol. 32, pp. 13212–13219.

    Article  CAS  PubMed  Google Scholar 

  8. Schramm, V.L., J. Biol. Chem., 2007, vol. 282, pp. 28297–28300.

    Article  CAS  PubMed  Google Scholar 

  9. Silva, R.G., Hirschi, J.S., Ghanem, M., Murkin, A.S., and Schramm, V.L., Biochemistry, 2011, vol. 50, pp. 2701–2709.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Konstantinova, I.D., Fateev, I.V., and Miroshnikov, A.I., RF Patent No. 2480218, 2013.

    Google Scholar 

  11. Konstantinova, I.D., Fateev, I.V., Galegov, G.A., Deryabin, P.G., Botikov, A.G., Muzyka, I.S., L’vov, D.K., and Miroshnikov, A.I., Russ. J. Bioorg. Chem., 2013, vol. 39, no. 5, pp. 530–538.

    Article  CAS  Google Scholar 

  12. Jensen, K.F. and Nygaard, P., Eur. J. Biochem., 1975, vol. 51, pp. 253–265.

    Article  CAS  PubMed  Google Scholar 

  13. Berzin, V.B., Dorofeeva, E.V., Leonov, V.N., and Miroshnikov, A.I., Russ. J. Bioorg. Chem., 2009, vol. 35, no. 2, pp. 193–196.

    Article  CAS  Google Scholar 

  14. Mehellou, Y., Balzarini, J., and McGuigan, C., Antiviral Chem. Chemother., 2010, vol. 20, pp. 153–160.

    Article  CAS  Google Scholar 

  15. Konstantinova, I.D., Antonov, K.V., Fateev, I.V., Miroshnikov, A.I., Stepchenko, V.A., Baranovsky, A.V., and Mikhailopulo, I.A., Synthesis, 2011, no. 10, pp. 1555–1560.

    Google Scholar 

  16. Esipov, R.S., Gurevich, A.I., Chuvikovsky, D.V., Chupova, L.A., Muravyova, T.I., and Miroshnikov, A.I., Protein Expr. Purif., 2002, vol. 24, no. 1, pp. 56–60.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997, Russia

    I. D. Konstantinova, I. V. Fateev & A. I. Miroshnikov

Authors
  1. I. D. Konstantinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Fateev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. Miroshnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. D. Konstantinova.

Additional information

Original Russian Text © I.D. Konstantinova, I.V. Fateev, A.I. Miroshnikov, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 4, pp. 411–420.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Konstantinova, I.D., Fateev, I.V. & Miroshnikov, A.I. The arsenolysis reaction in the biotechnological method of synthesis of modified purine β-D-arabinonucleosides. Russ J Bioorg Chem 42, 372–380 (2016). https://doi.org/10.1134/S1068162016040105

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162016040105

Keywords

Search

Navigation