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Uridine, Thymidine and Inosine Used as Chiral Stationary Phases in HPLC
Corresponding Author(s) : Li-Ming Yuan
Asian Journal of Chemistry,
Vol. 26 No. 8 (2014): Vol 26 Issue 8
Abstract
In this paper, we present the first enantioseparations research using thymidine, uridine and inosine as chiral stationary phase bonded to silica gel via 3-(triethoxysilyl)propyl isocyanate in HPLC. Thymidine and uridine chiral stationary phases possess enantioseparation selectivity for alcohols, amines, ketones and carboxylic acids to some degree in normal-phase and reversed-phase mode. This work indicates that nucleoside or deoxynucleoside can be useful for the separation of enantiomers in the liquid phase as a new kind of chiral stationary phase.
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- P.T. Anastas and J.C. Warner, Green Chemistry Theory and Practice, Oxford University Press, New York, pp. 1-10 (1998).
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References
P.T. Anastas and J.C. Warner, Green Chemistry Theory and Practice, Oxford University Press, New York, pp. 1-10 (1998).
N.M. Maier, P. Franco and W. Lindner, J. Chromatogr. A, 906, 3 (2001); doi:10.1016/S0021-9673(00)00532-X.
W.Z. Sun and L.M. Yuan, J. Liq. Chromatogr. Relat. Technol., 32, 553 (2009); doi:10.1080/10826070802671549.
G. Gübitz and M.G. Schmid, Chiral Separations Methods and Protocols, Humana Press, NJ, pp. 1-36 (2004).
H.J. Choi and M.H. Hyun, J. Liq. Chromatogr. & Rel. Tech., 30, 853 (2007); doi:10.1080/10826070701191136.
Y.X. Chang, L.L. Zhou, G.X. Li, L. Li and L.M. Yuan, J. Liq. Chromatogr. & Rel. Tech., 30, 2953 (2007); doi:10.1080/10826070701589057.
C. Yamamoto and Y. Okamoto, Bull. Chem. Soc. Jpn., 77, 227 (2004); doi:10.1246/bcsj.77.227.
D.W. Armstrong and W. DeMond, J. Chromatogr. Sci., 22, 411 (1984); doi:10.1093/chromsci/22.9.411.
D.W. Armstrong, T.J. Ward, R.D. Armstrong and T.E. Beesley, Science, 232, 1132 (1986); doi:10.1126/science.3704640.
M.L. Ma, C.H. Ren, Y.J. Lv, H. Chen and X.J. Li, Chin. Chem. Lett., 22, 155 (2011); doi:10.1016/j.cclet.2010.09.025.
M. Padmanaban, P. Muller, C. Lieder, K. Gedrich, R. Grunker, V. Bon, I. Senkovska, S. Baumgartner, S. Opelt, S. Paasch, E. Brunner, F. Glorius, E. Klemm and S. Kaskel, Chem. Commun., 47, 12089 (2011); doi:10.1039/c1cc14893a.
A.L. Nuzhdin, D.N. Dybtsev, K.P. Bryliakov, E.P. Talsi and V.P. Fedin, J. Am. Chem. Soc., 129, 12958 (2007); doi:10.1021/ja076276p.
A. Higuchi, H. Yomogita, B.O. Yoon, T. Kojima, M. Hara, S. Maniwa and M. Saitoh, J. Membr. Sci., 205, 203 (2002); doi:10.1016/S0376-7388(02)00113-8.
Y. Matsuoka, N. Kanda, Y.M. Lee and A. Higuchi, J. Membr. Sci., 280, 116 (2006); doi:10.1016/j.memsci.2006.01.013.
M. Michaud, E. Jourdan, A. Villet, A. Ravel, C. Grosset and E. Peyrin, J. Am. Chem. Soc., 125, 8672 (2003); doi:10.1021/ja034483t.
J. Ruta, C. Ravelet, C. Grosset, J. Fize, A. Ravel, A. Villet and E. Peyrin, Anal. Chem., 78, 3032 (2006); doi:10.1021/ac060033i.
J.Y. Wang, F. Zhao, M. Zhang, Y. Peng and L.M. Yuan, Chin. Chem. Lett., 19, 1248 (2008); doi:10.1016/j.cclet.2008.07.003.
R. Aburatani, Y. Okamoto and K. Hatada, Bull. Chem. Soc. Jpn., 63, 3606 (1990); doi:10.1246/bcsj.63.3606.
B. Chankvetadze, M. Saito, E. Yashima and Y. Okamoto, Chirality, 10, 134 (1998); doi:10.1002/chir.21.