Skip to main content
Log in

Synthesis of paricalcitol: A novel strategy combining chemical and microbial transformations

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

Abstract

A novel strategy was developed for the preparation of paricalcitol (1α,25-dihydroxy-19-norvitamin D2) via seven-step chemical transformation and one-step microbial transformation. Using vitamin D2 as a starting material, 1α- and 25-hydroxyl groups of paricalcitol were introduced by Pseudonocardia autotrophica CGMCC5098 at the late stage of the synthesis, allowing us to avoid harsh reaction conditions and tedious steps. The overall yield of paricalcitol was 0.75%.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Fraser, D.R. and Kodicek, E., Nature, 1970, vol. 228, pp. 764–766.

    Article  CAS  PubMed  Google Scholar 

  2. DeLuca, H.F. and Schnoes, H.K., Annu. Rev. Biochem., 1983, vol. 52, pp. 411–439.

    Article  CAS  PubMed  Google Scholar 

  3. Ikekawa, N., Med. Res. Rev., 1987, vol. 7, pp. 333–366.

    Article  CAS  PubMed  Google Scholar 

  4. DeLuca, H.F., Vitamin D, 2nd ed., Feldman D., Pike, J.W., and Glorieux, F.H., Eds., New York: Academic Press, 2005.

    Google Scholar 

  5. Noboru, K., Curr. Bioact. Compd., 2006, vol. 2, pp. 301–315.

    Article  Google Scholar 

  6. Kubodera, N., Molecules, 2009, vol. 14, p. 3869.

    Article  CAS  PubMed  Google Scholar 

  7. Sintov, A. C., Yarmolinsky, L., Dahan, A., and Ben-Shabat, S., Drug Discov. Today, 2014, vol. 19, pp. 1769–1774.

    Article  CAS  PubMed  Google Scholar 

  8. Jones, G., Annu. Rev. Nutr., 2013, vol. 33, pp. 23–44.

    Article  CAS  PubMed  Google Scholar 

  9. Kulesza, U., Sigüeiro, R., Mouriño, A., and Sicinski, R. R., J. Org. Chem., 2013, vol. 78, pp. 1444–1450.

    Article  CAS  PubMed  Google Scholar 

  10. Kabat, M. M. and Radinov, R., Curr. Opin. Drug Discov. Dev., 2001, vol. 4, pp. 808–833.

    CAS  Google Scholar 

  11. Goldenberg, M. M., Clin. Ther., 1999, vol. 21, pp. 432–441.

    Article  CAS  PubMed  Google Scholar 

  12. Trillini, M., Cortinovis, M., Ruggenenti, P., Reyes Loaeza, J., Courville, K., Ferrer-Siles, C., Prandini, S., Gaspari, F., Cannata, A., Villa, A., Perna, A., Gotti, E., Caruso, M. R., Martinetti, D., Remuzzi, G., and Perico, N., J. Am. Soc. Nephrol., 2015, vol. 26, pp. 1205–1214.

    Article  CAS  PubMed  Google Scholar 

  13. Bover, J., DaSilva, I., Furlano, M., Lloret, M. J., Diaz-Encarnacion, M.M., Ballarin, J., and Cozzolino, M., Curr. Vasc. Pharmacol., 2014, vol. 12, pp. 313–323.

    Article  CAS  PubMed  Google Scholar 

  14. Toyoda, A., Nagai, H., Yamada, T., Moriguchi, Y., Abe, J., Tsuchida, T., and Nagasawa, K., Tetrahedron, 2009, vol. 65, pp. 10002–10008.

    Article  CAS  Google Scholar 

  15. Kubodera, N., J. Syn. Org. Chem. Jpn., 2010, vol. 68, pp. 904–910.

    Article  CAS  Google Scholar 

  16. Kubodera, N., Heterocycles, 2010, vol. 80, pp. 83–98.

    Article  CAS  Google Scholar 

  17. Li, L., Yue, L., Xue, J., Xie, Z., and Li, Y., Chinese Sci. Bull., 2012, vol. 57, pp. 1616–1619.

    Article  CAS  Google Scholar 

  18. Pietraszek, A., Malińska, M., Chodyński, M., Krupa, M., Krajewski, K., Cmoch, P., Woźniak, K., and Kutner, A., Steroids, 2013, vol. 78, pp. 1003–1014.

    Article  CAS  PubMed  Google Scholar 

  19. Deng, Z., People Rep. China Pat., Faming Zhuanli Shenqing, 2014, vol. CN 103896817.

    Google Scholar 

  20. Li, Y., Xue, J., Zhang, X. and Xu, S., Peope Rep. China Pat., Faming Zhuanli Shenqing, 2010, vol. CN 101880253.

    Google Scholar 

  21. Bader, T., Stutz, A., Bichsel, H.-U., and Fu, C., Universitat Zurich Pat., PCT Int. Appl. no. WO 2010009879, 2010.

    Google Scholar 

  22. Chodynski, M., Krupa, M., Krajewski, K., Kubiszewski, M., Kutner, A., Pietraszek, A., and Trzcinska, K., PCT Int. Appl., no. WO 2011016739, 2010.

    Google Scholar 

  23. Kutner, A., Perlman, K. L., Lago, A., Schnoes, H.K., DeLuca, H.F., and Sicinski, R.R., J. Org. Chem., 1988, vol. 53, pp. 3450–3457.

    Article  CAS  Google Scholar 

  24. Lu, Q., Feng, H., Wen, P., Sun, B., Wan, Y., and Zhou, A., People Rep. China Pat no. CN 102392053, Faming Zhuanli Shenqing, 2012.

    Google Scholar 

  25. Fujii, Y. and Tamura, T., PCT Int. Appl. no. WO 2007138894, 2007.

    Google Scholar 

  26. Machida, K., Ito, S. F., Yoshikazu, Hirosue, S., and Arisawa, A., PCT Int. Appl. no. WO 2008096695, 2008.

    Google Scholar 

  27. Song, W.-Q., Wang, Y.-H., Liu, D.-N., Fang, W.-Z., and Lu, Q., Russ. J. Gen. Chem., 2016, vol. 86, pp. 173–177.

    Article  CAS  Google Scholar 

  28. Wan, Y., Wen, P., Zhang, P., and Lu, Q., Chin. J. Org. Chem., 2012, vol. 32, pp. 1988–1992.

    Article  CAS  Google Scholar 

  29. Paaren, H.E., DeLuca, H.F., and Schnoes, H.K., J. Org. Chem., 1980, vol. 45, pp. 3253–3258.

    Article  CAS  Google Scholar 

  30. Perlman, K.L., Sicinski R.R., Schnoes, H.K., and DeLuca, H.F., Tetrahedron Lett., 1990, vol. 31, pp. 1823–1824.

    Article  CAS  Google Scholar 

  31. Ding, J., Guo, X., Zeng, Z., and Liu, N., Synlett. 2013, vol. 24, pp. 2606–2608.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to W. Z. Fang or Q. Lu.

Additional information

The article is published in the original.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Luo, J.Q., Jiang, F., Song, W.Q. et al. Synthesis of paricalcitol: A novel strategy combining chemical and microbial transformations. Russ J Bioorg Chem 43, 323–327 (2017). https://doi.org/10.1134/S1068162017030104

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162017030104

Keywords

Navigation