Review High-performance liquid chromatographic enantioseparation of drugs containing multiple chiral centers on chiral stationary phases

Authors

1 Department of Chemistry, Faculty of Sciences, K.N. Toosi University of Technology, Tehran, Iran

2 Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Iran

Abstract

In recent years there has been considerable interest in the synthesis and separation of enantiomers of organic compounds especially because of their importance in the biochemistry and pharmaceutical industry. High-performance liquid Chromatography is a very useful method for the direct separation of enantiomers. However, about 30−40 years ago, commercially available chiral stationary phases were very limited. Researchers developed many novel chiral stationary phases for gas and liquid chromatography, and found these phases were effective practically to the separation and analysis of various chiral compounds. Enantioseparation of drugs with multiple chiral centers is challenging. This review describes resolution of some drugs with multiple chiral centers using polysaccharide-type chiral stationary phases.

Keywords


[1] V.A. Davankov, Pure Appl. Chem. 69 (1997) 1469.
[2] H.Y. Aboul-Enein, J. Chromatogr. A 906 (2001) 185
[3] H.Y. Aboul-Enein, L.I. Abou-Basha, Chirality and Drug Hazards, in: H.Y. Aboul-Enein, I.W. Wainer (Eds.), The Impact of Stereochemistry on Drug Development and Use, Wiley, New York, 1997.
[4] S. Levin, S. Abu-Lafi, The Role of Enantioselective Liquid Chromatographic Separations Using Chiral Stationary Phases in Pharmaceutical Analysis, in Advances in Chromatography. E. Grushka, P.R. Brown, Eds., Marcel Dekker Inc.: NY, Vol. 33, 1993.
[5] D. R. Taylor, K. Maher, J. Chromatogr. Sci. 30 (1992) 67.
[6] G. Gubitz, Chromatographia 30 (1990) 555.
[7] E. Gil−Av, B. Feibush, R. Charles−Sigler, Tetrahedron Lett. 10 (1966) 1009.
[8] V.A. Davankov, S.V. Rogozhin, J. Chromatogr. 60 (1971) 280.
[9] N. Oi, Chromatography 26 (2005) 1.
[10] M. Schulte, R. Devant, R. Grosser, J. Pharm. Biomed. Anal. 27 (2002) 627.
[11] (a) R.M. Nicoud, Pharm. Technol. Eur. 11 (3) (1999) 36, (b) R.M. Nicoud, Pharm. Technol. Eur. 11 (1999) 28.
[12] M. Schulte, J. Strube, J. Chromatogr. 906 (2001) 399.
[13] B. Chankvetadze, I. Kartozia, C. Yamamoto, Y. Okamoto, J. Pharm. Biomed. Anal. 27 (2002) 467.
[14] S.C. Ng, L. Chen, L.F. Zhangb, C.B. Chingc, Tetrahedron Lett. 43 (2002) 677.
[15] L. Chen, L.F. Zhang, C.B. Ching, S.C. Ng, J. Chromatogr. A 950 (2002) 65.
[16] Y. Song, D. Wang, Y. Hu, X. Chen, Y. Jiao, D. Hou, J. Pharm. Biomed. Anal. 31 (2003) 311.
[17] R. Cirilli, R. Costi, R. Di Santo, M. Artico, A. Roux, B. Gallinella, L. Zanitti, F. La Torre, J. Chromatogr. A 993 (2003) 17.
[18] M.G. Schmid, N. Grobuschek, V. Pessenhofer, A. Klostius, G. Gu¨bitz, J. Chromatogr. A 990 (2003) 83.
[19] T. Wang, R.M. Wenslow, J. Chromatogr. A 1015 (2003) 99.
[20] X. Zhang, J. Ouyang, W.R.G. Baeyens, S. Zhai, Y. Yang, G. Huang, J. Pharm. Biomed. Anal. 31 (2003) 1047.
[21] N. Mesplet, Y. Saito, P. Morin, L.A. Agrofoglio, J. Chromatogr. A 983 (2003) 115
[22] X. Lai, S.C. Ng, Tetrahedron Lett. 44 (2003) 2657.
[23] F. Bachmann, J. Hopken, R. Koli, D. Lohmann, J. Schneider, J. Carbohydr. Chem. 17 (1998) 1359.
[24] X. Chen, Y. Liu, F. Qin, L. Kong, H. Zou, J. Chromatogr. A 1010 (2003) 185.
[25] M.M. Hefnawy, H.Y. Aboul-Enein, J. Pharm. Biomed. Anal. 35 (2004) 535.
[26] Pharmaceutical Information Associates, Ltd. (PIA), Medical Sciences Bulletin, September 1997.
[27] Z. Zhang, G. Yang, G. Liang, H. Liu, Y. Chen, J. Pharm. Biomed. Anal. 34 (2004) 689.
[28] K. Pihlainen, R. Kostiainen, J. Chromatogr. A 1033 (2004) 91.
[29] K. Gyimesi-Forras, J. Kokosi, G. Szasz, A. Gergely, W. Lindner, J. Chromatogr. A 1047 (2004) 59.
[30] G.S. Yang, S.L. Yuan, X.J. Lin, Z.N. Qi, C.B. Liu, H.Y. Aboul-Enein, G. Félix, Talanta 64 (2004) 320.
[31] X.H. Lai, S.C. Ng, J. Chromatogr. A 1031 (2004) 135.
[32] L.D. Melton, K.N. Slessor, Carbohydr. Res. 18 (1971) 29.
[33] K. Takahashi, K. Hatorri, F. Toda, Tetrahedron Lett. 25 (1984) 3331.
[34] F. Bachmann, J. Hopken, R. Koli, D. Lohmann, J. Schneider, J. Carbohydr. Chem. 9 (1998) 1359.
[35] C. Ravelet, M. Michaud, A. Ravel, C. Grosset, A. Villet, E. Peyrin, J. Chromatogr. A 1036 (2004) 155.
[36] X. Chen, F. Qin, Y. Liu, X. Huang, H. Zou, J. Chromatogr. A 1034 (2004) 109.
[37] W. Kang, D.J. Lee, K.H. Liu, Y.E. Sunwoo, K.I. Kwon, I.J. Cha, J.G. Shin, J. Chromatogr. B 814 (2005) 75.
[38] Z.D. Zhai, Y.P. Shi, T. Wang, Anal. Chim. Acta 550 (2005) 123.
[39] F. Pellati, S. Benvenuti, M. Melegari, J. Pharm. Biomed. Anal. 37 (2005) 839.
[40] T. Zhang, M. Schaeffer, P. Franco, J. Chromatogr. A 1083 (2005) 96.
[41] G. D’Orazio, Z. Aturki, M. Cristalli, M.G. Quaglia, S. Fanali, J. Chromatogr. A 1081 (2005) 105.
[42] R. Nageswara Rao, A. Narasa Raju, D. Nagaraju, J. Pharm. Biomed. Anal. 42 (2006) 347.
[43] Y. Okamoto, E. Yashima, Angew. Chem. Int. Ed. 37 (1998) 1020.
[44] Y. Okamoto, Y. Kaida, J. Chromatogr. A 666 (1994) 403.
[45] I.W.Wainer, R.M. Stiffin, T. Shibata, J. Chromatogr. 411 (1987) 139.
[46] E. Yashima, Y. Okamoto, Bull. Chem. Soc. Jpn. 68 (1995) 3289.
[47] R. Torok, A. Bor, G. Orosz, F. Lukacs, D.W. Armstrong, A. Peter, J. Chromatogr. A 1098 (2005) 75.
[48] A. Ghanem, H. Hoenen, H.Y. Aboul-Enein, Talanta 68 (2006) 602.
[49] M. Juza, M. Mazzotti, M. Morbidelli, Trends Biotech. 18 (2000) 108.
[50] V.d. Veredas, M.J.S. Carpes, C.R.D. Correia, C.C. Santana, J. Chromatogr. A 1119 (2006) 156.
[51] J.A. Sellers, B.A. Olsen, P.K. Owens, P.F. Gavin, J. Pharm. Biomed. Anal. 41 (2006) 1088.
[52] R.N. Rao, D. Nagaraju, A.N. Raju, J. Pharm. Biomed. Anal. 41 (2006) 766.
[53] M. Morii, H. Takata, H. Fujisaki, N. Takeguchi, Biochem. Pharmacol. 39 (1990) 661.
[54] M. Rabinson, J. Horn, Drugs 63 (2003) 2739.
[55] R.N. Rao, A.N. Raju, D. Nagaraju, Talanta 70 (2006) 805.
[56] T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber, T.J. Mitchinson, Science 286 (1999) 971.
[57] A. Cavazzini, A. Massi, G. Bergamaschi, S. Braga, F. Dondi, F. Dondoni, Biotechnol. Progr. 20 (2004) 603.
[58] O.P. Kleidernigg, C.O. Kappe, Tetrahedron: Asymmetry 8 (1997) 2057.
[59] G. Nadalini, F. Dondi, A. Massi, A. Dondoni, T. Zhang, A. Cavazzini, J. Chromatogr. A 1126 (2006) 357.
[60] M. Beaufour, P. Morin, J.P. Ribet, J.C. Maurizot, J. Pharm. Biomed. Anal. 41 (2006) 544.
[61] M. Beaufour, Ph. Morin, J.P. Ribet, J. Sep. Sci. 28 (2005) 529.
[62] E.Z. Abdel-Moety, K.A. Al-Rashood, in: K. Florey (Ed.), Analytical Profiles of Drug Substance, vol. 18, Academic Press, New York, 1988.
[63] C.N. Svendsen, M. Froimowitz, C. Hrbek, A. Campbell, N. Kula, R.J. Baldessarini, B.M. Cohen, S. Babb, M.H. Teicher, E.D. Bird, Neuropharmacology 27 (1988) 1117.
[64] S.A. Jortani, A. Poklis, J. Anal. Toxicol. 17 (1993) 374.
[65] R. Bhushan, Deepak Gupta, J. Chromatogr. B 837 (2006) 133.
[66] E.P. Sousa, A.M.S. Silva, M.M.M. Pinto, M.M. Pedro, F.A.M. Cerqueira, M.S.J. Nascimento, Helv. Chim. Acta 85 (2002) 2862.
[67] L. Saraiva, P. Fresco, E. Pinto, E. Sousa, M. Pinto, J. Goncalves, J. Enzyme Inhib. Med. Chem. 18 (2003) 357.
[68] E.P. Sousa, M.E. Tiritan, R.V. Oliveira, C.M.M. Afonso, Q.B. Cass, M.M.M. Pinto, Chirality 16 (2004) 279.
[69] M.E. Sousa, M.E. Tiritan, K.R.A. Belaz, M. Pedro, M.S.J. Nascimento, Q.B.Cass, M.M.M. Pinto, J. Chromatogr. A 1120 (2006) 75.
[70] M. Khan, B. Viswanathan, D.S. Rao, R. Reddy, J. Chromatogr. B 846 (2007) 119.
[71] C.V. Gonc¸alves, M.J.S. Carpes, C.R.D. Correa, C.C. Santana, Chem. Eng. J. 133 (2007) 151.
[72] M.M. Hefnawy, M.A. Sultan, M.M. Al-Shehri, J. Chromatogr. B 856 (2007) 328.
[73] C.V. Hoffmann, M. Laemmerhofer, W. Lindner, J. Chromatogr. A 1161 (2007) 242.