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Vol. 31 No. 1 (2019): Vol 31 Issue 1

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A New Synthetic Route for Preparation of Enantiomers of Gossypol and Apogossypol from Racemic Gossypol

https://doi.org/10.14233/ajchem.2019.21580
Vu Dinh Tien
School of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, Vietnam
Vu Van Vu
School of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, Vietnam
Tran Khac Vu
School of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, Vietnam

Corresponding Author(s) : Tran Khac Vu

vu.trankhac@hust.edu.vn

Asian Journal of Chemistry, Vol. 31 No. 1 (2019): Vol 31 Issue 1

Abstract

The paper described the preparation of enantiomers of gossypol and apogossypol from racemic gossypol via a two-step procedure. In the first step, D-tryptophan methyl ester was used as an effective agent to resolve racemic gossypol into (–)-gossypol and (+)-gossypol. Next, the deformylation reaction of the corresponding (–)-gossypol and (+)-gossypol was conducted in sodium hydroxide solution, followed by sulfuric acid neutralization in inert atmosphere and the resulting precipitate was filtered and washed with water to give (–)-apogossypol and (+)-apgossypol, respectively in high yields and in high enantiomeric excesses.

Keywords

Racemic (–)-Gossypol ( )-Gossypol D-Tryptophan methyl ester (–)-Apogossypol ( )-Apogossypol
Tien, V. D., Vu, V. V., & Vu, T. K. (2018). A New Synthetic Route for Preparation of Enantiomers of Gossypol and Apogossypol from Racemic Gossypol. Asian Journal of Chemistry, 31(1), 105–108. https://doi.org/10.14233/ajchem.2019.21580
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References
  1. C.L. Oliver, J.A. Bauer, K.G. Wolter, M.L. Ubell, A. Narayan, K.M. O’Connell, S.G. Fisher, S. Wang, X. Wu, M. Ji, T.E. Carey and C.R. Bradford, Clin. Cancer Res., 10, 7757 (2004); https://doi.org/10.1158/1078-0432.CCR-04-0551.
  2. M. Zhang, H. Liu, Z. Tian, B.N. Griffith, M. Ji and Q.Q. Li, Life Sci., 80, 767 (2007); https://doi.org/10.1016/j.lfs.2006.11.004.
  3. R.M. Mohammad, S. Wang, S. Banerjee, X. Wu, J. Chen and F.H. Sarkar, Pancreas, 31, 317 (2005); https://doi.org/10.1097/01.mpa.0000179731.46210.01.
  4. M. Zhang, H. Liu, R. Guo, Y. Ling, X. Wu, B. Li, P.P. Roller, S. Wang and D. Yang, Biochem. Pharmacol., 66, 93 (2003); https://doi.org/10.1016/S0006-2952(03)00248-X.
  5. D.W. Hahn, C. Rusticus, A. Probst, R. Homm and A.N. Johnson, Contraception, 24, 97 (1981); https://doi.org/10.1016/0010-7824(81)90072-X.
  6. J. Yang, G. Chen, L.L. Li, W. Pan, F. Zhang, J. Yang, S. Wu and P. Tien, Bioorg. Med. Chem. Lett., 23, 2619 (2013); https://doi.org/10.1016/j.bmcl.2013.02.101.
  7. J. Yang, F. Zhang, J.R. Li, G. Chen, S.W. Wu, W.J. Ouyang, W. Pan, R. Yu, J.X. Yang and P. Tien, Bioorg. Med. Chem. Lett., 22, 1415 (2012); https://doi.org/10.1016/j.bmcl.2011.12.076.
  8. R.J. Radloff, L.M. Deck, R.E. Royer and D.L. Vander Jagt, Pharmacol. Res. Commun., 18, 1063 (1986); https://doi.org/10.1016/0031-6989(86)90023-8.
  9. G. Tegos, F.R. Stermitz, O. Lomovskaya and K. Lewis, Antimicrob. Agents Chemother., 46, 3133 (2002); https://doi.org/10.1128/AAC.46.10.3133-3141.2002.
  10. J. Qiu, L.K. Levin, J. Buck and M.M. Reidenberg, Exp. Biol. Med., 227, 398 (2002); https://doi.org/10.1177/153537020222700605.
  11. G. Tang, C.-Y. Yang, Z. Nikolovska-Coleska, J. Guo, S. Qiu, R. Wang, W. Gao, G. Wang, J. Stuckey, K. Krajewski, S. Jiang, P.P. Roller and S. Wang, J. Med. Chem. Lett., 50, 1723 (2007);https://doi.org/10.1021/jm061400l.
  12. X.S. Liang, A.J. Rogers, C.L. Webber, T.J. Ormsby, M.E. Tiritan, S.A. Matlin and C.C. Benz, Invest. New Drugs, 13, 181 (1995); https://doi.org/10.1007/BF00873798.
  13. S. Kitada, C.L. Kress, M. Krajewska, L. Jia, M. Pellecchia and J.C. Reed, Blood, 111, 3211 (2008); https://doi.org/10.1182/blood-2007-09-113647.
  14. L. Coward, G. Gorman, P. Noker, C. Kerstner-Wood, M. Pellecchia, J.C. Reed and L. Jia, J. Pharm. Biomed. Anal., 42, 581 (2006); https://doi.org/10.1016/j.jpba.2006.05.020.
  15. J. Wei, J.L. Stebbins, S. Kitada, R. Dash, W. Placzek, M.F. Rega, B. Wu, J. Cellitti, D. Zhai, L. Yang, R. Dahl, P.F. Fisher, J.C. Reed and M. Pellecchia, J. Med. Chem., 53, 4166 (2010); https://doi.org/10.1021/jm1001265.
  16. J. Wei, S. Kitada, M.F. Rega, J.L. Stebbins, D. Zhai, J. Cellitti, H. Yuan, A. Emdadi, R. Dahl, Z. Zhang, L. Yang, J.C. Reed and M. Pellecchia, J. Med. Chem., 52, 4511 (2009); https://doi.org/10.1021/jm900472s.
  17. J. Wei, M.F. Rega, S. Kitada, H. Yuan, D. Zhai, P. Risbood, H.H. Seltzman, C.E. Twine, J.C. Reed and M. Pellecchia, Cancer Lett., 273, 107 (2009); https://doi.org/10.1016/j.canlet.2008.07.031.
  18. J. Wei, S. Kitada, M.F. Rega, A. Emdadi, H. Yuan, J. Cellitti, J.L. Stebbins, D. Zhai, J. Sun, L. Yang, R. Dahl, Z. Zhang, B. Wu, S. Wang, T.A. Reed, N. Lawrence, A. Sebti, J.C. Reed and M. Pellecchia, Mol. Cancer Ther., 8, 904 (2009); https://doi.org/10.1158/1535-7163.MCT-08-1050.
  19. A.I. Meyers and J.J. Willemsen, Chem. Commun., 16, 1573 (1997); https://doi.org/10.1039/a703043f.
  20. R. Chandrashekar, A.K. Kumar, Y.R. Reddy and P.J. Chaitanyal, J. Pharmacogn. Phytochem., 2, 180 (2013).
  21. H.X. Jiang, X.X. Cao, H. Huang and B. Jiang, Tetrahedron Asymm., 18, 2437 (2007); https://doi.org/10.1016/j.tetasy.2007.09.032.
  22. L.T. Xoan, N.T.T. Trang, N.T. Ha, N.V. Quang and N.V. Tai, J. Med. Mater., 15, 149 (2010) (in Vietnamese).
  23. S.A. Matlin, A. Belenguer, R.G. Tyson and A.N. Brookes, J. High Resolut. Chromatogr. Chromatogr. Commun., 10, 86 (1987); https://doi.org/10.1002/jhrc.1240100207.
  24. E.P. Clark, J. Biol. Chem., 58, 159 (1928).
  25. L.J. Powers and P.H. Dorsett, J. Label. Comp. Radiopharm., 17, 309 (1980); https://doi.org/10.1002/jlcr.2580170219
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