Preparation and Enantioseparation Property of Chiral Stationary Phases Based on Cellulose Tris(3,5-dimethylbenzoate)─A New Way to Prepare Polysaccharide-coating Type Chiral Stationary Phases

Wei Chen Rong Duan Qing-chun Fan Zheng-wu Bai Shao-hua Huang

Citation:  Wei Chen, Rong Duan, Qing-chun Fan, Zheng-wu Bai, Shao-hua Huang. Preparation and Enantioseparation Property of Chiral Stationary Phases Based on Cellulose Tris(3,5-dimethylbenzoate)─A New Way to Prepare Polysaccharide-coating Type Chiral Stationary Phases[J]. Chinese Journal of Polymer Science, 2014, 32(4): 458-466. doi: 10.1007/s10118-014-1409-x shu

Preparation and Enantioseparation Property of Chiral Stationary Phases Based on Cellulose Tris(3,5-dimethylbenzoate)─A New Way to Prepare Polysaccharide-coating Type Chiral Stationary Phases

  • 基金项目:

    This work was financially supported by the National Natural Science Foundation of China (No. 50973086) and Hubei Provincial Department of Education of China (Z 20081501).

摘要: A new method to prepare polysaccharide-coating type chiral stationary phases (CSPs) was developed in this work. As a typical example, naked silica gel was coated by cellulose, which was then derivatized with 3,5-dimethylbenzoyl chloride to afford cellulose tris(3,5-dimethylbenzoate)-silica gel (CTDBS) complex. The silanols on CTDBS were end-capped with 3-aminopropyltriethoxysilane to obtain CSP 1. The amino groups on CSP 1 were further end-capped with 3,5-dimethylbenzoyl chloride to give CSP 2. The silanols on CTDBS were end-capped with methyltrimethoxysilane to yield CSP 3. CSPs 1-3 were characterized by FTIR, solid-state 13C-NMR and elemental analysis. The enantioseparation abilities of CSPs 1-3 were evaluated with structurally various chiral analytes. The enantioseparation results demonstrated that the end-capping moieties on CSPs 1 and 2 significantly affected enantioseparation. In addition, the effect of the structures of chiral analytes and end-capping moieties on the retention factors and the resolutions was discussed.

English


    1. [1]

      Beesley, T.E. and Lee J[J].T., J. Liq. Chromatogr. Related Technol.2009, 32:1733-[2]Zhang, C.H, Wang, H.L, Liu, F.B., Shen, X.D., Liu, L.J., Sakai, R., Satoh, T., Kakuchi, T. and Okamoto, Y., Acta PolymericaSinica, 2013, (6): 811[3]Andersson.[J].S. In: Chiral Separation Techniques, Subramanian, G. Ed, WileyVCHVerlag GmbH Co. KGaA.2007,:-[4]Bai, J.W., Shen, X.D., Liu, W.B., Zhang, C.H., Xiao, H. and Xu, X.D., Acta Polymerica Sinica, 2013, (4): 419[5]Luo, M., Zhang, J. and Wan, X.H., Acta Polymerica Sinica, 2013, (4): 443[6]Zhang, Y., Wu, D[J].R., WangIverson,D.B. and Tymiak, A.A., Drug discovery today.2005, 10:571-[7]Okamoto, Y., Aburatani, R[J].and Hatada K., J. Chromatogr.1987, 389:95-[8]Okamoto, Y., Kawashima, M[J].and Hatada, K., J. Chromatogr.1986, 363:173-[9]Shen, J., Ikai, T[J].and Okamoto, Y., J. Chromatogr. A.2010, 1217:1041-[10]Cancelliere, G., D'Acquarica, I[J]., Gasparrini, F., Misiti, D. and Villani, C., Pharm. Sci. Technol. Today.1999, 2:484-[11]Pirkle, W.H. and Koscho, M[J].E., J. Chromatogr. A.1999, 840:151-[12]Snyder, S.E., Carey, J.R. and Pirkle, W.H., Tetrahedron, 2005, 61: 7562[13]Han, X., He, L., Zhong, Q., Beesley, T. and Armstrong, D.W., Chromatographia, 2006, 63: 13[14]Zhong, Q., Han, X., He, L., Beesley, T.E., Trahanovsky, W.S. and Armstrong, D.W., J. Chromatogr. A, 2005, 1066: 55[15]Ali, I. and AboulEnein,H[J].Y., J. Sep. Sci.2006, 29:762-[16]Ikai, T. and Okamoto, Y[J]., Chem. Rev.2009, 109:6077-[17]Okamoto, Y., J. Polym[J].Sci., Part A: Polym. Chem.2009, 47:1731-[18]Chen, X. M., Yamamoto, C[J].and Okamoto, Y., J. Sep. Sci.2006, 29:1432-[19]Ikai, T., Yamamoto, C[J]., Kamigaito, M. and Okamoto, Y., J. Chromatogr. B.2008, 875:2-[20]Ikai, T., Yamamoto, C[J]., Kamigaito, M. and Okamoto, Y., J. Chromatogr. A.2007, 1157:151-[21]Tang, S., Ikai, T., Tsuji, M. and Okamoto, Y., Chirality, 2010, 22: 165[22]AboulEnein,H.Y., J[J].Chromatogr. A.2001, 906:185-[23]Ali, I., Saleem, K., Hussain, I., Gaitonde, V.D. and AboulEnein,H.Y., Sep. Purif. Rev., 2009, 38: 97[24]Huang, S.H., Bai, Z[J].W. and Feng, J.W., Magn. Reson. Chem.2009, 47:423-[25]Pirkle, W.H. and Readnour, R[J].S., Chromatographia.1991, 31:129-[26]Pirkle, W.H. and Pochapsky, T[J].C., Chem. Rev.1989, 89:347-[27]Berthod, A., Anal. Chem., 2006, 78: 2093

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  • 发布日期:  2014-04-05
  • 收稿日期:  2013-07-08
  • 修回日期:  2013-07-29
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