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Use of organic modifiers to enhance chiral selectivity in capillary electrophoresis

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Summary

Using capillary electrophoresis, the enantiomers of a number of dansyl amino acids were resolved using nativeβ-cyclodextrin. The neutral chiral host resolved analytes possessing a negative charge at pH 9, the conditions employed in this study. Organic modifiers added to the running buffer were particularly adept at enhancing chiral recognition between the guest and host molecule in capillary electrophoresis. This work examined the effects of methanol, dimethylformamide, and acetonitrile on the resolution, migration time, and efficiency of twelve dansyl amino acids. Examples are given of the separation of racemic dansyl amino acids utilizing this technique and conditions necessary to achieve enantioselectivity.

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References

  • Ahuja S (1991) Chiral separations by liquid chromatography. ACS Symposium Series 471, ACS, Washington DC

    Google Scholar 

  • Altria KD, Goodall DM, Rogan MM (1992) Chiral separation ofβ-amino alcohols by capillary electrophoresis using cyclodextrins as buffer additives I. Effect of varying operating parameters. Chromatographia 34: 19–24

    Google Scholar 

  • Ariens EJ, Wuis EW (1987) Bias in pharmacokinetics and clinical pharmacology. Clin Pharmacol Ther 42: 361–363

    Google Scholar 

  • Armstrong DW, Li W, Pitha J (1990a) Reversing enantioselectivity in capillary gas chromatography with polar and nonpolar cyclodextrin derivative phases. Anal Chem 62: 214–217

    Google Scholar 

  • Armstrong DW, Bertrand GL, Ward KD, Ward TJ, Secor H, Seeman J (1990b) Evaluation of the effect of organic modifier and pH on retention and selectivity in reversed phase liquid chromatographic separation of alkaloids on a cyclodextrin bonded phase. Anal Chem 62: 332–338

    Google Scholar 

  • Cruzado ID, Vigh G (1992) Chiral separations by capillary electrophoresis using cyclodextrin-containing gels. J Chromatogr 608: 421–425

    Google Scholar 

  • Fanali S (1989) Separation of optical isomers by capillary zone electrophoresis based on host-guest complexation with cyclodextrins. J Chromatogr 474: 441–446

    Google Scholar 

  • Fanali S (1991) Use of cyclodextrins in capillary electrophoresis: resolution of terbutaline and propranolol enantiomers. J Chromatogr 545: 437–444

    Google Scholar 

  • Fanali S, Bocek P (1990) Enantiomeric resolution by using capillary zone electrophoresis: resolution of racemic tryptophan and determination of the enantiomer composition of commercial pharmaceutical epinephrine. Electrophoresis 11: 757–760

    Google Scholar 

  • FDA's policy statement for the development of new stereoisomeric drugs (1992) Chirality 45: 338–340

    Google Scholar 

  • Nardi A, Ossicini L, Fanali S (1992) Use of cyclodextrins in capillary zone electrophoresis for the separation of optical isomers: resolution of racemic tryptophan derivatives. Chirality 4: 56–61

    Google Scholar 

  • Schurig V, Nowotny HP (1988) Separation of enantiomers on diluted permethylatedβ-cyclodextrin by high-resolution gas chromotography. J Chromatogr 441: 155–163

    Google Scholar 

  • Sepaniak MJ, Cole RO, Clark BK (1992) Use of native and chemically modified cyclodextrins for the capillary electrophoretic separation of racemates. J Liqu Chromatogr 15: 1023–1040

    Google Scholar 

  • Tanaka M, Yoshinaga M, Asano S, Yamashoji Y, Kawaguchi Y (1992) Enantiomeric separation of dansylamino acids by capillary zone electrophoresis based on complexation with cyclodextrins. Fresenius' J Anal Chem 343: 896–900

    Google Scholar 

  • Terabe S, Otsuka K, Ichikawa K, Tsuchiya A, Ando T (1984) Electrokinetic separations with micellar solutions and open-tubular capillaries. Anal Chem 56: 111–113

    Google Scholar 

  • Terabe S, Hiroto O, Otsuka K, Ando T (1985) Electrokinetic chromatography with micellar solutions. Separation of PTH-amino acids. J Chromatogr 332: 219–226

    Google Scholar 

  • Ward TJ, Armstrong DW (1988) Cyclodextrin-stationary phases. In: Crane LJ, Zief M (eds) Chromatographic chiral separations, vol 40. Marcel Dekker, New York, pp 131–163

    Google Scholar 

  • Wren SA, Rowe RC (1992) Theoretical aspects of chiral separations in capillary electrophoresis: I. Initial evaluation of a model. J Chromatogr 603: 235–241

    Google Scholar 

  • Yoshinaga M, Asano S, Tanaka M, Toshiyuki S (1991) Separation of racemates by capillary zone electrophoresis based on complexation with cyclodextrin derivatives. Anal Sci 7: 257–260

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Millsaps College, 1701 N. State St., 39210, Jackson, Mississippi, USA

    T. J. Ward, M. Nichols, L. Sturdivant & C. C. King

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  1. T. J. Ward
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  2. M. Nichols
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  3. L. Sturdivant
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  4. C. C. King
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Ward, T.J., Nichols, M., Sturdivant, L. et al. Use of organic modifiers to enhance chiral selectivity in capillary electrophoresis. Amino Acids 8, 337–344 (1995). https://doi.org/10.1007/BF00806551

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  • DOI: https://doi.org/10.1007/BF00806551

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