中文
Announcement
More
Progress in Chemistry 2014, Vol. 26 Issue (0203): 415-423 DOI: 10.7536/PC130776 Previous Articles   Next Articles

• Review •

Progress in Preparation and Applications of Cellulose Derivatives-Based Chiral Stationary Phase

Weng Xilun, Bao Zongbi*, Luo Fei, Su Baogen, Yang Yiwen, Ren Qilong   

  1. Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China
  • Received: Revised: Online: Published:
  • Supported by:

    The work was supported by the National Natural Science Foundation of China (No.21006083,21376205)

PDF ( 1350 ) Cited
Export

EndNote

Ris

BibTeX

Preparation of optically pure isomers and determination of the enantiomeric excess of chiral racemates are becoming increasingly important. Nowadays, many top selling drugs around the world have been administrated as single enantiomer with its desired physiological effect. Direct enantioseparation using chiral stationary phases (CSPs) by high performance liquid chromatography (HPLC) has signicantly evolved during the past few decades and has been recognized as the most popular and reliable tool for both analysis and preparation purposes.This paper reviewed the recent progress and breakthroughs made on the preparation of CSPs based on cellulose derivatives as selector. The new approaches for preparing the coated-type, bonded-type and hybrid-type CSPs are specifically discussed and evaluated. Many attempts to clarify the chiral recognition mechanism of cellulose derivatives-based CSPs on liquid chromatography have been carried out by NMR spectroscopy, ATR-FTIR, X-ray analysis and DFT etc. Apart from HPLC, the polysaccharide-based CSPs have also been used for simulated moving bed (SMB) and supercritical fluid chromatography (SFC), which are well-established techniques and becoming potential alternative for production of single enantiomer drugs. The applications performed by SFC and SMB are also summarized, and the purities, productivities and solvent consumptions are specifically displayed.Moreover, future prospects on design of new chiral selectors and optimization of supporting medium of CSPs based on cellulose derivatives are presented.

Contents
1 Introduction
2 Classification and preparation methods
2.1 Coated-type CSPs
2.2 Bonded-type CSPs
2.3 Organic-inorganic hybrid CSPs
3 Chiral discrimination mechanism
4 Application
5 Outlook

CLC Number: 

[1] Okamoto Y, Kawashima M, Hatada K. J. Chromatogr. A, 1986, 363: 173.
[2] Yashima E, Okamoto Y. Bull. Chem. Soc. Jpn., 1995, 68: 3289.
[3] Okamoto Y, Kaida Y. J. Chromatogr. A, 1994, 666: 403.
[4] Chen L M, Wang X S, Liu X, Jiang S X. Int. J. Polym. Anal. Charact., 2009, 14: 160.
[5] Katoh Y, Tsujimoto Y, Yamamoto C, Ikai T, Kamigaito M, Okamoto Y. Polym. J., 2010, 43: 84.
[6] Tang S W, Li X F, Wang F, Liu G H, Li Y L, Pan F Y. Chirality, 2012, 24: 167.
[7] McNeff C, Zigan L, Johnson K, Carr P W, Wang A, Weber-Main A M. LC GC North America, 2000, 18: 514.
[8] Kwon S H, Okamoto Y, Yamamoto C, Cheong W, Moon M, Park J H. Anal. Sci., 2006, 22: 1525.
[9] Kumar A P, Park J H. Anal. Lett., 2012, 45: 15.
[10] Kim M, Park J H. J. Chromatogr. A, 2012, 1251: 244.
[11] Kumar A P, Park J H. J. Chromatogr. A, 2011, 1218: 6548.
[12] Kumar A P, Park J H. J. Chromatogr. A, 2011, 1218: 5369.
[13] Ge J, Zhao L, Shi Y P. Chin. J. Chem., 2008, 26: 139.
[14] 杜明霞(Du M X), 徐茂震(Xu M Z), 绍鑫(Shao X), 蒲锡鹏(Pu X P), 李文智(Li W Z). 化学学报(Acta Chim. Sin.), 2011, 69: 2746.
[15] Francotte E. Chiral Separations, Applications and Technology, Washington DC: American Chemical Society, 1997. 271.
[16] Kouni H O, Ichida A. J. Chromatogr. A, 1995, 694: 91.
[17] Chankvetadze B. J. Chromatogr. A, 2012, 1269: 26.
[18] Okamoto Y, Ikai T, Shen J. Isr. J. Chem., 2011, 51: 1096.
[19] Chen X M, Yamamoto C, Okamoto Y. Pure Appl. Chem., 2007, 79: 1561.
[20] Ali I, AL-Othman Z A, Aboul-Enein H Y. Chiral Separations. Springer, 2013, 127.
[21] Okamoto Y, Aburatani R, Miura S I, Hatada K. J. Liq. Chromatogr., 1987, 10: 1613.
[22] Ling F, Brahmachary E, Xu M, Svec F, Frechet J M. J. Sep. Sci., 2003, 26: 1337.
[23] Tang S, Liu G, Li X, Jin Z, Wang F, Pan F, Okamoto Y. J. Sep. Sci., 2011, 34: 1763.
[24] Chen X M, Yamamoto C, Okamoto Y. J. Chromatogr. A, 2006, 1104: 62.
[25] Chen X M, Yamamoto C, Okamoto Y. J. Sep. Sci., 2006, 29: 1432.
[26] Seo Y J, Kang G W, Park S T, Moon M, Park J H, Cheong W J. Bull. Korean Chem. Soc., 2007, 28: 999.
[27] Zhang S, Ong T T, Ng S C, Chan H S O. Tetrahedron. Lett., 2007, 48: 5487.
[28] Shemper B S, Mathias L J. Eur. Polym. J., 2004, 40: 651.
[29] Zhang L, Cheng Z, Shi S, Li Q, Zhu X. Polymer, 2008, 49: 3054.
[30] Braunecker W A, Brown W C, Morelli B C, Tang W, Poli R, Matyjaszewski K. Macromolecules, 2007, 40: 8576.
[31] Tsujii Y, Ohno K, Yamamoto S, Goto A, Fukuda T, Surface-Initiated Polymerization I. Heidelberg: Springer Berlin, 2006. 1.
[32] Xie M, Kong Y, Han H, Shi J, Ding L, Song C, Zhang Y. React. Funct. Polym., 2008, 68: 1601.
[33] Meng T, Gao X, Zhang J, Yuan J, Zhang Y, He J. Polymer, 2009, 50: 447.
[34] Hu D, Cheng Z, Zhu J, Zhu X. Polymer, 2005, 46: 7563.
[35] Ishizu K, Murakami T, Takano S. J. Colloid Interf. Sci., 2008, 322: 59.
[36] Yang J H, Choi S H. J. Appl. Polym. Sci., 2012, 127: 4122.
[37] Matrab T, ChancolonJ, L'hermite M M, Rouzaud J N, Deniau G, Boudou J P, Chehimi M M, Delamar M. Colloid. Surface A, 2006, 287: 217.
[38] Bae I, Park J, Choi S. Polym. Int., 2011, 60: 833.
[39] Yang J, Choi S. J. Appl. Polym. Sci., 2011, 122: 3016.
[40] Ikai T, Yamamoto C, Kamigaito M, Okamoto Y. Chem. Lett., 2006, 35: 1250.
[41] Ikai T, Yamamoto C, Kamigaito M, Okamotoc Y. J. Chromatogr. B, 2008, 875: 2.
[42] Ikai T, Yamamoto C, Kamigaito M, Okamoto Y. J. Chromatogr. A, 2007, 1157: 151.
[43] Tang S, Ikai T, Tsuji M, Okamoto Y. Chirality, 2010, 22: 165.
[44] Li J Q, Ikai T, Okamoto Y. J. Sep. Sci., 2009, 32: 2885.
[45] Sugiura Y, Yamamoto C, Ikai T, Kamigaito M, Okamoto Y. Polym. J., 2010, 42: 31.
[46] Shen J, Ikai T, Okamoto Y. J. Chromatogr. A, 2010, 1217: 1041.
[47] Tang S, Ikai T, Tsuji M, Okamoto Y. J. Sep. Sci., 2010, 33: 1255.
[48] Qu H T, Li J Q, Wu G S, Shen J, Shen X, Okamoto Y. J. Sep. Sci., 2011, 34: 536.
[49] Sanchez C, Ribot F. New J. Chem., 1994, 18: 1007.
[50] Schottner G. Chem. Mater., 2001, 13: 3422.
[51] Avnir D, Coradin T, Lev O, Livage J. J. Mater. Chem., 2006, 16: 1013.
[52] Fidalgo A, Ciriminna R, Ilharco L M, Pagliaro M. Chem. Mater., 2005, 17: 6686.
[53] Rebbin V, Schmidt R, Froba M. Angew. Chem. Int. Edit., 2006, 45: 5210.
[54] Zhong H, Zhu G, Yang J, Wang P, Yang Q. Microporous Mesoporous Mat., 2007, 100: 259.
[55] Inagaki S, Guan S, Ohsuna T, Terasaki O. Nature, 2002, 416: 304.
[56] Kapoor M P, Inagaki S. Chem. Lett., 2004, 33: 88.
[57] Kapoor M P, Yang Q, Inagaki S. Chem. Mater., 2004, 16: 1209.
[58] Wahab M, Imae I, Kawakami Y, Ha C S. Chem. Mater., 2005, 17: 2165.
[59] Camarota B, Onida B, Goto Y, Inagaki S, Garrone E. Langmuir, 2007, 23: 13164.
[60] Cho E B, Kim D, Jaroniec M. Langmuir, 2007, 23: 11844.
[61] Ikai T, Muraki R, Yamamoto C, Kamigaito M, Okamoto Y. Chem. Lett., 2004, 33: 1188.
[62] Ikai T, Yamamoto C, Kamigaito M, Okamoto Y. J. Sep. Sci., 2007, 30: 971.
[63] Ikai T, Okamoto Y. Chem. Rev., 2009, 109: 6077.
[64] Ikai T, Yamamoto C, Kamigaito M, Okamoto Y. Chem Asian J., 2008, 3: 1494.
[65] Chen X, Yamamoto C, Okamoto Y. Pure App. Chem., 2007, 79: 1561.
[66] Okamoto Y, Ikai T. Chem. Soc. Rev., 2008, 37: 2593.
[67] Kasat R B, Wang N H L, Franses E I. Biomacromolecules, 2007, 8: 1676.
[68] Kasat R B, Wang N H L, Franses E I. J. Chromatogr. A, 2008, 1190: 110.
[69] Tsui H W, Willing J N, Kasat R B, Wang N H L, Franses E I. J. Phys. Chem. B, 2011, 115: 12785.
[70] Scriba G K E. Chiral Separations. Springer, 2013. 1.
[71] Kasat R B, Wee S Y, Loh J X, Wang N H L, Franses E I. J. Chromatogr. B, 2008, 875: 81.
[72] Kasat R B, Franses E I, Wang N H L. Chirality, 2010, 22: 565.
[73] Cavazzini A, Pasti L, Massi A, Marchetti N, Dondi F. Analytica Chimica Acta, 2011, 706: 205.
[74] Uccello-Barretta G, Vanni L, Balzano F. J. Chromatogr. A, 2010, 1217: 928.
[75] Friebolin V, Marten S, Albert K. Magn. Reson. Chem., 2010, 48: 111.
[76] Ciogli A, Bicker W, Lindner W. Chirality, 2009, 22: 463.
[77] Yao B, Zhan F, Yu G, Chen Z, Fan W, Zeng X, Zeng Q, Weng W. J. Chromatogr. A, 2009, 1216: 5429.
[78] Zhan F, Yu G, Yao B, Guo X, Liang T, Yu M, Zeng Q, Weng W. J. Chromatogr. A, 2011, 1217: 4278.
[79] Aranyi A, Ilisz I, Pataj Z, Szatmâri I, Fülöp F, Armstrong D W, Péter A. Chirality, 2011, 23: 549.
[80] Cirilli R, Alcaro S, Fioravanti R, Secci D, Fiore S, La Torre F, Ortuso F. J. Chromatogr. A, 2009, 1216: 4673.
[81] Francotte E R. J. Chromatogr. A, 2001, 906: 379.
[82] Bao Z, Su B, Xing H, Yang Y, Ren Q. J. Sep. Sci., 2010, 33: 3256.
[83] Su B, Bao Z, Xing H, Yang Y, Ren Q. J. Chromatogr. A, 2009, 1216: 5140.
[84] Ribeiro A E, Gomes P S, Pais L S, Rodrigues A E. Chirality, 2011, 23: 602.
[85] Ribeiro A E, Gomes P S, Pais L S, Rodrigues A E. Sep. Sci. Technol., 2011, 46: 1726.
[86] Goncalves C V, Carpes M J S, Correia C R D, Santana C C. Biochem. Eng. J., 2008, 40: 526.
[87] Zabka M, Minceva M, Gomes P S, Rodrigues A E. Sep. Sci. Technol., 2008, 43: 727.
[88] Francotté E, Leutert T, La Vecchia L, Ossola F, Richert P, Schmidt A. Chirality, 2002, 14: 313.
[89] Acetti D, Langel C, Brenna E, Fuganti C, Mazzotti M. J. Chromatogr. A, 2010, 1217: 2840.
[90] Miller L. J. Chromatogr. A, 2012, 1250: 250.
[91] Guiochon G, Tarafder A. J. Chromatogr. A, 2011, 1218: 1037.
[92] Yan T Q, Orihuela C, Swanson D. Chirality, 2008, 20: 139.
[93] Qian-Cutrone J, Dasgupta B, Kozlowski E S, Dalterio R, Wang-Iverson D, Vrudhula V M. J. Pharm. Biomed. Anal., 2008, 48: 1120.
[94] Yan T Q, Orihuela C, Preston J P, Xia F. Chirality, 2010, 22: 922.
[95] Gahm K H, Tan H, Liu J, Barnhart W, Eschelbach J, Notari S, Thomas S, Semin D, Cheetham J. J. Pharm. Biomed. Anal., 2008, 46: 831.
[96] Rajendran A. Curr. Opin. Chem. Eng., 2013, 2: 263.
[97] Kaemmerer H, Horvath Z, Lee J W, Kaspereit M, Arnell R, Hedberg M, Herschend B, Jones M J, Larson K, Lorenz H, Seidel-Morgensten A. Org. Process Res. Dev., 2012, 16: 331.
[98] Langermann J, Kaspereit M, Shakeri M, Lorenz H, Hedberg M, Jones M J, Larson K, Herschend B, Arnell R, Temmel E, Bäckvall J E, Kienle A, Seidel-Morgenstern A. Org. Process Res. Dev., 2012, 16: 343.
[99] Chen J, Duan R, Chen W, Zhang J, Luo X G, Li J, Bai Z W. Curr. Anal. Chem., 2013, 9: 128.
[100] Tamura K, Sam N S M, Ikai T, Okamoto Y, Yashima E. Bull. Chem. Soc. Jpn., 2011, 84: 741.
[101] Han Y, Zhou Z, Wu H, Nie H, Lei R, Bai Y, Liu H. J. Chromatogr. A, 2012, 1235: 125.
[102] [KG*2]Kasprzyk-Hordern B. Chem. Soc. Rev., 2010, 39: 4466.

[1] Liu Chuanfu Zhang Aiping Li Weiying Sun Runcang. Dissolution of Cellulose in Novel Green Solvent Ionic Liquids and Its Application [J]. Progress in Chemistry, 2009, 21(09): 1800-1806.
[2] Gao Yongfeng Yuan Jinying Sui Xiaofeng Zhou Mi Cai Zhinan. Electrospinning of Cellulose and Cellulose Derivatives [J]. Progress in Chemistry, 2009, 21(0708): 1553-1559.
[3] Li Li,Zi Min,Ren Chaoxing,Yuan Liming **. The Development of Chiral Stationary Phase in Gas Chromatography [J]. Progress in Chemistry, 2007, 19(0203): 393-403.
[4] Yongzhu He1,3|Hao Pang1,3|Bing Liao1,2*. Progress in Cellulose-Based Chiral Stationary Phases [J]. Progress in Chemistry, 2006, 18(0708): 957-965.
[5] Huang Yong. Recent Advances in Liquid Crystals of Cellulose and Its Derivatives [J]. Progress in Chemistry, 1997, 9(02): 209-.