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Application of Native and Hydroxypropyl-Substituted β-Cyclodextrin Bonded Silica Gel as Stationary Phases for High Performance Liquid Chromatography

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Abstract

Two chiral stationary phases for high-performance liquid chromatography (HPLC) have been synthesized by grafting native and 2-hydroxypropyl-β-cyclodextrin onto silica gel by a previously described method. They were tested under reversed-phase conditions. These two materials enable separation of the enantiomers of a variety of drugs (benzodiazepine anxiolytics, arylpropionic acids, anti-inflammatory and anticoagulant agents) and herbicides (aryloxyphenoxypropionic esters). Both chiral stationary phases enabled good chiral recognition in reversed-phase mode. The effects of the nature and composition of the mobile phase, of compound structure (mechanisms of chiral discrimination), and of flow-rate were studied.

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References

  • FDA (1992) Chirality 4:338–340

    Google Scholar 

  • Kubo Y, Hirota N, Maeda S, Tokita S (1998) Anal Sci 14:183–189

    Article  CAS  Google Scholar 

  • Weber K, Kreuzig R, Bahadir M (1997) Chemosphere 35(1/2):13–20

    Google Scholar 

  • Otsuka K, Smith CJ, Grainger J, Barr JR, Patterson DG, Tanaka N, Terabe S (1998) J Chromatogr A 817:75–81

    Article  CAS  Google Scholar 

  • Sánchez-Rasero F, Matallo MB, Dios G, Romero E, Peña A (1998) J Chromatogr A 799:355–360

    Google Scholar 

  • Hegeman WJM, Laane RWPM (2002) Environ Toxicol Chem 173:85–116

    Google Scholar 

  • Yashima E (2001) J Chromatogr A 906:105–125

    Article  CAS  Google Scholar 

  • Ng SC, Ong TT, Fu P, Ching CB (2002) J Chromatogr A 968:31–40

    Article  CAS  Google Scholar 

  • Makino Y, Urano Y, Nagano T (2002) J Chromatogr A 947:151–154

    Article  CAS  Google Scholar 

  • Garcés J, Franco P, Oliveros L, Minguillon C (2003) Tetrahedron Asymmetry 14:1179–1185

    Google Scholar 

  • Schmid MG, Gecse O, Szabo Z, Kilar F, Gubitz G, Ali I, Aboul-Enein HY (2001) J Liq Chromatogr Related Technol 24(16):2493–2504

    Article  CAS  Google Scholar 

  • Iha MH, Martinez AS, Bonato PS (2002) J Chromatogr B 767:1–9

    Article  CAS  Google Scholar 

  • Nakagama T, Hirasawa K, Uchiyama K, Hobo T (2001) Anal Sci 17:119–124

    Article  CAS  Google Scholar 

  • Xu M, Brahmachary E, Janco M, Ling FH (2001) J Chromatogr A 928:25–40

    Article  CAS  Google Scholar 

  • Okamoto Y, Yashima E (1997) In: Hatada K, Kitayama T, Vogl O (eds) Macromolecular design of polymeric materials, Marcel Dekker, New York

  • Perrin C, Matthijs N, Mangelings D, Granier-Loyaux C, Maftouh M, Massart DL, Vander Heyden Y (2002) J Chromatogr A 966:119–134

    Article  CAS  Google Scholar 

  • Chankvetadze B, Chankvetadze L, Sidamonidze S, Kasashima E, Yashima E, Okamoto Y (1997) J Chromatogr A 787:67–77

    Article  CAS  Google Scholar 

  • Simms PJ, Jeffries CT, Zhao X, Huang Y, Arrhenius T (2004) J Chromatogr A 1052:69–75

    Article  CAS  Google Scholar 

  • Soukup RJ, Rozhkov RV, Larok RC, Armstrong DW (2005) Chromatographia 61:219–224

    Article  CAS  ISI  Google Scholar 

  • Han X, Zhong Q, Yue D, Della Cà N, Larock RC, Armstrong DW (2005) Chromatographia 61:205–211

    Article  CAS  ISI  Google Scholar 

  • Lai XH, Ng SC (2004) J Chromatogr A 1031:135–142

    CAS  Google Scholar 

  • Gong Y, Lee HK (2003) J Sep Sci 26:515–520

    CAS  Google Scholar 

  • Grobuschek N, Sriphong L, Schmid MG, Lorand T, Aboul-Enein HY, Gubitz G (2002) J Biochem Biophys Methods 53:25–36

    Article  CAS  Google Scholar 

  • Lecnik O, Schmid MG, Kappe CO, Gübitz G (2001) Electrophoresis 22:3198–3202

    Article  CAS  ISI  Google Scholar 

  • Juvancz Z (2002) Trends Anal Chem 21(5):379–388

    Article  CAS  Google Scholar 

  • Cheng Y, Fan L, Chen H, Chen X, Hu Z (2005) J Chromatogr A 1072:259–265

    Article  CAS  Google Scholar 

  • McGachy NT, Grinberg N, Variankaval N (2005) J Chromatogr A 1064:193–204

    Article  CAS  Google Scholar 

  • Kim M, Way JD, Baldwin RM (2004) Korean J Chem Eng 21(2):465–468

    CAS  Google Scholar 

  • Armstrong DW, DeMond W (1984) J Chromatogr Sci 22:411–415

    CAS  Google Scholar 

  • Mitchell CR, Armstrong DW (2003) In: Gübitz G, Schmid MG (eds) Chiral separations methods and protocols, Humana Press, Totowa, New Jersey

  • Pino V, Afonso AM, González V, Hinze WL (2003) J Liq Chromatogr Related Technol 26(1):1–15

    Article  CAS  Google Scholar 

  • Herraez-Hernandez R, Campins-Falco P (2001) Anal Chim Acta 434:315–324

    Article  CAS  Google Scholar 

  • Kim H, Radwanski E, Lovey R, Lin CC, Nomeir AA (2002) Chirality 14:436–441

    Article  CAS  ISI  Google Scholar 

  • Guillaume YC, Robert JF, Guinchard C (2001) Talanta 55:263–269

    Article  CAS  ISI  Google Scholar 

  • Rudaz S, Veuthey JL (1999) Chirality 11:319–325

    CAS  ISI  Google Scholar 

  • Leonelli F, Garofalo B, Migneco LM, Bettolo RM (2003) J Liq Chromatogr Related Technol 26(3):401–416

    Article  CAS  Google Scholar 

  • Fujimura K, Suzuki S, Hayashi K, Masuda S (1990) Anal Chem 62(20):2198–2205

    Article  CAS  Google Scholar 

  • Carbonnier B, Janus L, Lekchiri Y, Morcellet M (2004) J Chromatogr Sci 42:37–42

    CAS  Google Scholar 

  • Hargitai T, Kaida Y, Okamoto Y (1993) J Chromatogr 628:11–22

    Article  CAS  Google Scholar 

  • Nakamura K, Fujima H, Kitagawa H, Wada H, Makino K (1995) J Chromatogr A 694:111–118

    Article  CAS  Google Scholar 

  • Fujimura K, Kitagawa M, Takayanagi H, Ando T (1986) J Liq Chromatogr 9(2/3):607–620

    Google Scholar 

  • Tazerouti F, Badjah-Hadj-Ahmed AY, Meklati BY, Franco P, Minguillon C (2002) Chirality 14:59–66

    Article  CAS  ISI  Google Scholar 

  • Armstrong DW (2002) In: Issaq HJ (ed) Century of separation science, Marcel Dekker, New York

  • Stalcup AM, Chang SC, Armstrong DW (1990) J Chromatogr 513:181–194

    Article  CAS  Google Scholar 

  • Pellati F, Benvenuti S, Melegari M, Firenzuoli F (2002) J Pharm Biomed Anal 29:1113–1119

    Article  CAS  Google Scholar 

  • Kawaguchi Y, Tanaka M, Nakae M, Funazo K, Shono T (1983) Anal Chem 55:1852–1857

    Article  CAS  Google Scholar 

  • Astec (1997) Chiral separations, a guide to using cyclodextrin bonded phases for liquid chromatography, BAS Technicol, UK

  • Armstrong DW, Chang C-D, Lee SH (1991) J Chromatogr 539:83–90

    Article  CAS  Google Scholar 

  • Beeson MD, Vigh G (1993) J Chromatogr 634:197–204

    Article  CAS  Google Scholar 

  • Félix G, Cachau C, Thienpont A, Soulard MH (1996) Chromatographia 42(9/10):583–590

    Google Scholar 

  • Tesarova E, Bosakova Z (2003) J Sep Sci 26:661–668

    Article  CAS  Google Scholar 

  • Ward TJ, Armstrong DW (1988) In: Zief M, Crane LJ (eds) Chromatographic chiral separations, Marcel Dekker, New York

  • Hefnawy MM, Stewart JT (1999) Anal Lett 32(1):159–171

    CAS  Google Scholar 

  • Chen S (2001) J Chin Chem Soc 48:751–756

    CAS  Google Scholar 

  • Schuster A, Götte C, Bernhardt G, Buschauer A (2001) Chirality 13:285–293

    Article  CAS  ISI  Google Scholar 

  • Ng SC, Ong TT, Fu P, Ching CB (2002) J Chromatogr A 968:31–40

    Article  CAS  Google Scholar 

  • Trapp O, Trapp G, Schurig V (2002) J Biochem Biophys Methods 54:301–313

    Article  CAS  Google Scholar 

  • Trapp O, Schoetz G, Schurig V (2001) Chirality 13:403–414

    Article  CAS  ISI  Google Scholar 

Download references

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Correspondence to F. Tazerouti.

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Revised: 7 July and 29 September 2005

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Ahmed, K.S., Tazerouti, F., Badjah-Hadj-Ahmed, A.Y. et al. Application of Native and Hydroxypropyl-Substituted β-Cyclodextrin Bonded Silica Gel as Stationary Phases for High Performance Liquid Chromatography. Chroma 62, 571–579 (2005). https://doi.org/10.1365/s10337-005-0673-x

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  • DOI: https://doi.org/10.1365/s10337-005-0673-x

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