Advertisement

Russian Journal of Bioorganic Chemistry

, Volume 43, Issue 3, pp 323–327 | Cite as

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

  • J. Q. Luo
  • F. Jiang
  • W. Q. Song
  • W. Z. FangEmail author
  • Q. LuEmail author
Article
  • 41 Downloads

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%.

Keywords

paricalcitol vitamin D2 microbial transformation chemical synthesis 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Fraser, D.R. and Kodicek, E., Nature, 1970, vol. 228, pp. 764–766.CrossRefPubMedGoogle Scholar
  2. 2.
    DeLuca, H.F. and Schnoes, H.K., Annu. Rev. Biochem., 1983, vol. 52, pp. 411–439.CrossRefPubMedGoogle Scholar
  3. 3.
    Ikekawa, N., Med. Res. Rev., 1987, vol. 7, pp. 333–366.CrossRefPubMedGoogle Scholar
  4. 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. 5.
    Noboru, K., Curr. Bioact. Compd., 2006, vol. 2, pp. 301–315.CrossRefGoogle Scholar
  6. 6.
    Kubodera, N., Molecules, 2009, vol. 14, p. 3869.CrossRefPubMedGoogle Scholar
  7. 7.
    Sintov, A. C., Yarmolinsky, L., Dahan, A., and Ben-Shabat, S., Drug Discov. Today, 2014, vol. 19, pp. 1769–1774.CrossRefPubMedGoogle Scholar
  8. 8.
    Jones, G., Annu. Rev. Nutr., 2013, vol. 33, pp. 23–44.CrossRefPubMedGoogle Scholar
  9. 9.
    Kulesza, U., Sigüeiro, R., Mouriño, A., and Sicinski, R. R., J. Org. Chem., 2013, vol. 78, pp. 1444–1450.CrossRefPubMedGoogle Scholar
  10. 10.
    Kabat, M. M. and Radinov, R., Curr. Opin. Drug Discov. Dev., 2001, vol. 4, pp. 808–833.Google Scholar
  11. 11.
    Goldenberg, M. M., Clin. Ther., 1999, vol. 21, pp. 432–441.CrossRefPubMedGoogle Scholar
  12. 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.CrossRefPubMedGoogle Scholar
  13. 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.CrossRefPubMedGoogle Scholar
  14. 14.
    Toyoda, A., Nagai, H., Yamada, T., Moriguchi, Y., Abe, J., Tsuchida, T., and Nagasawa, K., Tetrahedron, 2009, vol. 65, pp. 10002–10008.CrossRefGoogle Scholar
  15. 15.
    Kubodera, N., J. Syn. Org. Chem. Jpn., 2010, vol. 68, pp. 904–910.CrossRefGoogle Scholar
  16. 16.
    Kubodera, N., Heterocycles, 2010, vol. 80, pp. 83–98.CrossRefGoogle Scholar
  17. 17.
    Li, L., Yue, L., Xue, J., Xie, Z., and Li, Y., Chinese Sci. Bull., 2012, vol. 57, pp. 1616–1619.CrossRefGoogle Scholar
  18. 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.CrossRefPubMedGoogle Scholar
  19. 19.
    Deng, Z., People Rep. China Pat., Faming Zhuanli Shenqing, 2014, vol. CN 103896817.Google Scholar
  20. 20.
    Li, Y., Xue, J., Zhang, X. and Xu, S., Peope Rep. China Pat., Faming Zhuanli Shenqing, 2010, vol. CN 101880253.Google Scholar
  21. 21.
    Bader, T., Stutz, A., Bichsel, H.-U., and Fu, C., Universitat Zurich Pat., PCT Int. Appl. no. WO 2010009879, 2010.Google Scholar
  22. 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. 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.CrossRefGoogle Scholar
  24. 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. 25.
    Fujii, Y. and Tamura, T., PCT Int. Appl. no. WO 2007138894, 2007.Google Scholar
  26. 26.
    Machida, K., Ito, S. F., Yoshikazu, Hirosue, S., and Arisawa, A., PCT Int. Appl. no. WO 2008096695, 2008.Google Scholar
  27. 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.CrossRefGoogle Scholar
  28. 28.
    Wan, Y., Wen, P., Zhang, P., and Lu, Q., Chin. J. Org. Chem., 2012, vol. 32, pp. 1988–1992.CrossRefGoogle Scholar
  29. 29.
    Paaren, H.E., DeLuca, H.F., and Schnoes, H.K., J. Org. Chem., 1980, vol. 45, pp. 3253–3258.CrossRefGoogle Scholar
  30. 30.
    Perlman, K.L., Sicinski R.R., Schnoes, H.K., and DeLuca, H.F., Tetrahedron Lett., 1990, vol. 31, pp. 1823–1824.CrossRefGoogle Scholar
  31. 31.
    Ding, J., Guo, X., Zeng, Z., and Liu, N., Synlett. 2013, vol. 24, pp. 2606–2608.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  1. 1.Department of Сhemistry, School of Life Science and EngineeringSouthwest Jiaotong UniversityChengduChina

Personalised recommendations