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Separation of Enantiomers by Thin-Layer Chromatography

An Overview

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Chiral Separations

Part of the book series: Methods in Molecular Biology ((MIMB,volume 243))

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Abstract

The present review discusses the versatile applicability and separation mechanisms of thin-layer chromatographic enantiomeric separations. More detailed descriptions will be given for practical applications—separations of underivatized samples—on commercially available, ready-to-use plates, focusing on the thin-layer chromatographic racemate separation based on ligand exchange, which was introduced in 1983 by Günther et al. (1) and on use of a densitometer for determination of antipode distributions at trace level. This chapter will not discuss the numerous and interesting diastereomeric separations by paper and thin-layer chromatography (TLC). We refer to the literature on amino acids (28), peptides, diketopiperazines (918), and other classes of compounds (1931).

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References

  1. Günther, K., Martens, J., and Schickedanz, M. (1987) Verfahren zur dünnschicht-chromatographischen Trennung von Enantiomeren. EP-PS 143147, Degussa AG, Hanau, Germany.

    Google Scholar 

  2. Hardy, T. L. and Holland, D. O. (1952) The separation of DL-threonine from DL-allothreonine. Chem. and Ind. 855.

    Google Scholar 

  3. Shaw, K. N. F. and Fox, S. W. (1953) Stereochemistry of the β-phenylserines: improved preparation of allophenylserine. J. Am. Chem. Soc. 75, 3421–3424.

    CAS  Google Scholar 

  4. Drell, W. (1955) The separation of substituted threo-and erythro-phenylserines by paper chromatography. The configuration of arterenol and epinephrine. J. Am. Chem. Soc. 77, 5429–5431.

    CAS  Google Scholar 

  5. Piez, K. A., Irreverre, F., and Wolff, H. L. (1956) The separation and determination of cyclic imino acids. J. Biol. Chem. 233, 687–697.

    Google Scholar 

  6. Hegarty, M. P. (1957) The isolation and identification of 5-hydroxypiperidine-2-carboxylic acid from leucaena glauca benth. Aust. J. Chem. 10, 484–488.

    CAS  Google Scholar 

  7. Gray, D. O., Blake, J., Brown, D. H., and Fowden, L. (1964) Chromatographic separation of amino acid isomers. J. Chromatogr. 13, 276–277.

    PubMed  CAS  Google Scholar 

  8. Bellon, G., Berg, R., Chastang, F., Malgras, A., and Borel, J. P. (1984) Separation and evaluation of the cis and trans isomers of hydroxyprolines: effect of hydrolysis on the epimerisation. Anal. Biochem. 137, 151–155.

    PubMed  CAS  Google Scholar 

  9. Hinman, J. W., Caron, E. L., and Christensen, H. N. (1950) The isomeric dipeptides of valine including a correction. J. Am. Chem. Soc. 72, 1620–1625.

    CAS  Google Scholar 

  10. Sachs, H. and Brand, E. (1954) Optical rotation of peptides. VIII. Glutamic acid tripeptides. J. Am. Chem. Soc. 76, 1811–1814.

    CAS  Google Scholar 

  11. Taschner, E., Sokolowska, T., Biernat, J. F., Chimiak, A., Wasielewski, C., and Rzeszotarska, B. (1963) Aminosäuren und Peptide, XI. Nachweis der Racemisierung bei Peptidsynthesen durch Papierchromatographie. Liebigs Ann. Chem. 663, 197–202.

    CAS  Google Scholar 

  12. Sokolowska, T. and Biernat, J. F. (1964) The chromatographic separation of diastereoisomeric dipeptides. J. Chromatogr. 13, 269–270.

    PubMed  CAS  Google Scholar 

  13. Wieland, T. and Bende, H. (1965) Chromatographische Trennung einiger diastereomerer Dipeptide und Betrachtungen zur Konformation. Chem. Ber. 98, 504–515.

    CAS  Google Scholar 

  14. Nitecki, D. E., Halpern, B., and Westley, J. W. (1968) A simple route to sterically pure diketopiperazines. J. Org. Chem. 33, 864–866.

    CAS  PubMed  Google Scholar 

  15. Westley, J. W., Close, V. A., Nitecki, D. N., and Halpern, B. (1968) Determination of steric purity and configuration of diketopiperazines by gas-liquid chromatography, thin-layer chromatography, and nuclear magnetic resonance spectrometry. Anal. Chem. 40, 1888–1890.

    CAS  Google Scholar 

  16. Hubert, P. and Dellacherie, E. (1973) Thin-layer chromatographic separation of dipeptide and tripeptide diastereoisomers. J. Chromatogr. 80, 144–145.

    PubMed  CAS  Google Scholar 

  17. Arendt, A., Kolodziejczyk, B., and Sokolowska, T. (1976) Separation of diastereomers of protected dipeptides by thin-layer chromatography. Chromatographia 9, 123–126.

    CAS  Google Scholar 

  18. Lepri, L., Desideri, P. G., Heimler, D., and Giannessi, S. (1983) High-performance thin-layer chromatography of diastereomeric di-and tripeptides on ready-for-use plates of silanized silica gel and on ammonium tungstophosphate layers. J. Chromatogr. 265, 328–334.

    CAS  Google Scholar 

  19. Sarsúnová, M., Semonsky, M., and Cerny, A. (1970) Ergot alkaloids. XXXVI. Separation of diastereomeric (+)-1-hydroxy-2-butylamides of D-and L-lysergic and D-and L-isolysergic acids by thin-layer chromatography. J. Chromatogr. 50, 442–446.

    PubMed  Google Scholar 

  20. Sondack, D. L. (1974) TLC separation and identification of diastereomers of D-ergonovine maleate. J. Pharm. Sci. 63, 1141–1143.

    PubMed  CAS  Google Scholar 

  21. Giron, D. and Groel, I. P. (1978) Separation of diastereoisomers by reversed phase thin-layer chromatography. J. High Resol. Chromatogr. Chromatogr. Commun. 1, 67–68.

    CAS  Google Scholar 

  22. Kohli, J. C., Alang, N. K., and Khushminder, A. (1981) Specific separation of isopulegol from stereoisomeric isopulegols by thin layer chromatography. Sci. Cult. 47, 170.

    CAS  Google Scholar 

  23. Iida, T., Momose, T., Shinohara, T., Goto, J., Nambara, T., and Chang, F. C. (1986) Separation of allo bile acid stereoisomers by thin-layer and high-performance liquid chromatography. J. Chromatogr. 366, 396–402.

    PubMed  CAS  Google Scholar 

  24. Souter R. W. (1987) Chromatographic Separations of Stereoisomers. CRC Press, Boca Raton, pp. 212–221.

    Google Scholar 

  25. Palamareva, M. D., Haimova, M., Stefanovsky, J., Viteva, L., and Kurtev, B. (1971) Thin-layer chromatography on silica gel as a method for assigning the relative configurations to some aliphatic diastereomeric compounds. J. Chromatogr. 54, 383–391.

    CAS  Google Scholar 

  26. Palamareva, M. D. and Snyder, L. R. (1984) Liquid-solid chromatography of diastereomers: tetrasubstitutes ethanes. Chromatographia 19, 352–354.

    CAS  Google Scholar 

  27. Palamareva, M. D. (1988) Chromatographic behaviour of diastereomers. IX. Application of a microcomputer program to the thin-layer chromatographic separation of some diastereomers on silica. J. Chromatogr. 438, 219–224.

    CAS  Google Scholar 

  28. Palamareva, M. D., Kurtev, B. J., and Kavrakova, I. (1991) Chromatographic behaviour of diastereoisomers. X. Thin-layer chromatographic retentions on silica of some (E)-and (Z)-oxazolones and related cinnamates as a function of mobile phase effects or Hammett constants. J. Chromatogr. 545, 161–175.

    CAS  Google Scholar 

  29. Palamareva, M. D. and Kozekov, I. (1996) Theoretical threatment of the adsorptivity of esters of racemic and meso-2,3-dibromobutane-1,4-dioic acids on alumina. J. Planar Chromatogr. 9, 439–444.

    CAS  Google Scholar 

  30. Palamareva, M. D. and Kozekov, I. (1997) Chromatographic behaviour of diastereoisomers. XIII. Adsorptivity of esters of Z-and E-2,3-diphenylpropenoic acids and similar compounds on silica in terms of the Snyder theory. J. Chromatogr. A 758, 135–144.

    CAS  Google Scholar 

  31. Lippmann, T. and Mann, G. (1995) Chromatographie diastereomerer Calix[4] arene. Git Fachz. Lab. 3, 203–207.

    Google Scholar 

  32. Kotake, M., Sakan, T., Nakamura, N., and Senoh, S. (1951) Resolution into optical isomers of some amino acids by paper chromatography. J. Am. Chem. Soc. 73, 2973–2974.

    CAS  Google Scholar 

  33. Bonino, G. B. and Carassiti, V. (1951) Separation of the optical antipodes of racemic β-naphthol benzylamine by paper chromatography. Nature 167, 569–570.

    PubMed  CAS  Google Scholar 

  34. Berlingozzi, S., Serchi, G., and Adembri, G. (1951) Ricerche sugli aminoacidi rotatori.-Nota XII. Sperimentale. Sez. Chim. Biol. 2, 89–94.

    CAS  Google Scholar 

  35. Fujisawa, Y. (1951) Resolution of the racemic amino acids on the paper chromatograms. J. Osaka City Med. Center 1, 7–13.

    CAS  Google Scholar 

  36. Mason, M. and Berg, C. P. (1952) The metabolism of D-and L-tryptophan and D-and L-kynurenine by liver and kidney preparations. J. Biol. Chem. 195, 515–529.

    PubMed  CAS  Google Scholar 

  37. Dalgliesh, C. E. (1952) The optical resolution of aromatic amino acids on paper chromatograms. J. Chem. Soc. 3940–3942.

    Google Scholar 

  38. Closs, K. and Haug, C. M. (1953) Note on the resolution of DL-tryptophan by paper chromatography. Chem. Ind. 103.

    Google Scholar 

  39. Makino, K. and Takahashi, H. (1953) Synthesis of 5-hydroxykynurenine. Science 118, 699.

    PubMed  CAS  Google Scholar 

  40. Roberts, E. A. H. and Wood, D. J. (1953) Separation of tea polyphenols on paper chromatograms. Biochem. J. 53, 332–336.

    PubMed  CAS  Google Scholar 

  41. Lambooy, J. P. (1954) The syntheses, paper chromatography and substrate specificity for tyrosinase of 2,3-, 2,4-, 2,5-, 2,6-, and 3,5-dihydroxyphenylalanines. J. Chem. Am. Soc. 76, 133–138.

    CAS  Google Scholar 

  42. Weichert, R. (1954) Über Molekülverbindungen zwischen α-Aminosäuren und nicht-reduzierenden Zuckern. II. Acta Chem. Scand. 8, 1542–1546.

    CAS  Google Scholar 

  43. Berlingozzi, S., Adembri, G., and Bucci, G. (1954) Ricerche sugli aminoacidi rotatori.-Nota XVII. Sdoppiamento die D.L.forme per cromatografia su carta. Gazz. Chim. Ital. 84, 393–404.

    CAS  Google Scholar 

  44. Rhuland, L. E., Work, B., Denman, R. F., and Hoare, D. S. (1955) The behavior of the isomers of a,e-diaminopimelic acid on paper chromatograms. J. Am. Chem. Soc. 77, 4844–4846.

    CAS  Google Scholar 

  45. Hoare, D. S. and Work, B. (1955) The stereoisomers of α,ε-diaminopimelic acid: their distribution in nature and behaviour towards certain enzyme preparations. Biochem. J. 61, 562–568.

    PubMed  CAS  Google Scholar 

  46. Weichert, R. (1955) Spaltung von D,L-Histidin bei Papierchromatographie. Acta Chem. Scand. 9, 547.

    CAS  Google Scholar 

  47. Blaschko, H. and Hope, D. B. (1956) Excretion of cystathione in pyridoxine deficiency. Biochem. J. 63, 7P.

    Google Scholar 

  48. Klingmüller, V. and Maier-Sihle, L. (1957) Papierchromatographische Spaltung der racemischen Aminosäuren Histidin und Tryptophan. Z. Physiol. Chem. 308, 49–50.

    Google Scholar 

  49. Butenandt, A., Biekert, B., Koga, N., and Traub, P. (1960) Über Ommochrome, XXI. Konstitution und Synthese des Ommatins D. Z. Physiol. Chem. 321, 258–275.

    CAS  Google Scholar 

  50. Mayer, W. and Merger, F. (1961) Darstellung optisch aktiver Catechine durch Racemattrennung mit Hilfe der Adsorptionschromatographie an Cellulose. Liebigs Ann. Chem. 644, 65–69.

    CAS  Google Scholar 

  51. Kikkawa, I. (1961) Studies on the alkaloids of menispermaceous plants. CLXXXI. Optical resolution of dl-magnoflorine by paper chromatography. J. Pharm. Soc. Japan 81, 732–735.

    CAS  Google Scholar 

  52. Franck, B. and Schlingloff, G. (1962) Biogeneseähnliche Alkaloidsynthesen durch oxidative Kondensation, II. Synthese eines Aporphins. Liebigs Ann. Chem. 659, 123–132.

    CAS  Google Scholar 

  53. Tomita, M. and Sugamoto, M. (1962) Optical resolution of some alkaloids by paper chromatography and cellulose column chromatography. J. Pharm. Soc. Japan 82, 1141–1144.

    CAS  Google Scholar 

  54. De Ligny, C. L., Nieboer, H., De Vijlder, J. J. M., and van Willigen, J. H. H. G. (1963) Separation of some DL-amino acids into their optical isomers by paper adsorption chromatography. Recueil 82, 213–224.

    Google Scholar 

  55. Butenandt, A., Biekert, E., Kübler, H., and Linzen, B., and Traub, P. (1963) Über Ommochrome, XXII. Konstitution und Synthese des Rhodommatins. Z. Physiol. Chem. 334, 71–83.

    CAS  Google Scholar 

  56. Contractor, S. F. and Wragg, J. (1965) Resolution of the optical isomers of DL-tryptophan, 5-hydroxy-DL-tryptophan and 6-hydroxy-DL-tryptophan by paper and thin-layer chromatography. Nature 208, 71–72.

    PubMed  CAS  Google Scholar 

  57. Franck, B. and Blaschke, G. (1966) Biogeneseähnliche Alkaloidsynthesen durch oxydative Kondensation, VII. Neue Aporphin-Synthesen. Liebigs Ann. Chem. 695, 144–157.

    CAS  Google Scholar 

  58. Zaltzman-Nirenberg, P., Daly, J., Guroff, G., and Udenfriend, S. (1966) Separation of the enantiomers of the aminonaphthylalanines by paper chromatography. Anal. Biochem. 15, 517–522.

    PubMed  CAS  Google Scholar 

  59. Weichert, R. (1969) Zur Racemattrennung von Aminosäuren durch Papieradsorptionschromatographie. Ark Kemi 31, 517–532.

    CAS  Google Scholar 

  60. El Din Awad, A. M. and El Din Awad, O. M. (1974) Ion-exchange paper chromatographic resolution of some racemic DL-amino acids on alginate. J. Chromatogr. 93, 393–398.

    Google Scholar 

  61. Fu, Z., Sun, L., Cai, J., et al. (1997) Paper chromatographic separation of racemic diphenylmethyl alkohols using only pure water surfactant micellar mobile phase and host-guest chromatography. J. Chromatogr. Sci. 35, 309–314.

    CAS  Google Scholar 

  62. Kriz, D., Kriz, C. B., Andersson, L. I., and Mosbach, K. (1994) Thin-layer chromatography based on the molecular imprinting technique. Anal. Chem. 66, 2636–2639.

    CAS  Google Scholar 

  63. Suedee, R., Songkram, C., Petmoreekul, A., and Sangkunakup, S., Sankasa, S., and Kongyarit, N. (1998) Thin-layer chromatography using synthetic polymers imprinted with quinine as chiral stationary phase. J. Planar Chromatogr. 11, 272–276.

    CAS  Google Scholar 

  64. Suedee, R., Srichana, T., Saelim, J., and Thavornpibulbut, T. (1999) Chiral determination of various adrenergic drugs by thin layer chromatography using molecularly imprinted chiral stationary phases prepared with α-agonists. Analyst 124, 1003–1009.

    PubMed  CAS  Google Scholar 

  65. Suedee, R., Songkram, C., Petmoreekul, A., Sangkunakup, S., Sankasa, S., and Kongyarit, N. (1999) Direct enantioseparation of adrenergic drugs via thin-layer chromatography using molecularly imprinted polymers. J. Pharm. Biomed. Anal. 19, 519–527.

    PubMed  CAS  Google Scholar 

  66. Mack, M. and Kinkel, J. (1990) Trennmaterialien. DE 4005868, Merck Patent GmbH, Darmstadt, Germany.

    Google Scholar 

  67. Günther, K. and Möller, K. (1996) Separation of enantiomers by thin-layer chromatography. Handbook of Thin-Layer Chromatography, 2nd ed., Marcel Dekker, New York, pp. 621–682.

    Google Scholar 

  68. Haworth, D. T. and Hung, Y. W. (1973) Thin-layer chromatography of an optically active complex. J. Chromatogr. 78, 314–315.

    Google Scholar 

  69. Chimiak, A. and Polonski, T. (1975) Thin-layer chromatographic separation of diaminodicarboxylic acid stereoisomers and their dansyl derivatives. J. Chromatogr. 115, 635–638.

    PubMed  CAS  Google Scholar 

  70. Munier, R. L., Drapier, A. M., Gervais, C., and Tréfouël, J. (1976) Biochimie Analytique—Comportement des isoméres optiques du tryptophane et de ses analogues structuraux inhibiteurs de la croissance bactérienne en chromatographie sur cellulose à haute cristallinité. C. R. Acad. Sc. Paris, Ser. D 282, 1761–1764.

    CAS  Google Scholar 

  71. Bach, K. and Haas, H. J. (1977) Dünnschichtchromatographische Spaltung der Racemate einiger Aminosäuren. J. Chromatogr. 136, 186–188.

    PubMed  CAS  Google Scholar 

  72. Yuasa, S., Shimada, A., Kameyama, K., Yasui, M., and Adzuma, K. (1980) Cellulose thin-layer and column chromatography for resolution of DL-tryptophan. J. Chromatogr. Sci. 18, 311–314.

    CAS  Google Scholar 

  73. Yuasa, S. and Shimada, A. (1982) Separation of DL-amino acids by cellulose thin-layer chromatography. Sci. Rep. Osaka Univ. 31, 13–22.

    CAS  Google Scholar 

  74. Yuasa, S., Shimada, A., Isoyama, M., Fukuhara, T., and Itoh, M. (1986) Cellulose conformation responsible for resolution of DL-amino acids. Chromatographia 21, 79–82.

    CAS  Google Scholar 

  75. Wang, K. T., Chen, S. T., and Lo, L. C. (1986) The thin-layer chromatographic separation of enantiomeric dipeptides. Z. Anal. Chem. 324, 338–339.

    Google Scholar 

  76. Günther, K. and Zeller, M. Degussa AG, Hanau, Germany.

    Google Scholar 

  77. Kuhn, A. O., Lederer, M., and Sinibaldi, M. (1989) Adsorption chromatography on cellulose. IV. Separation of D-and L-tryptophan and D-and L-methyltryptophan on cellulose with aqueous solvents. J. Chromatogr. 469, 253–260.

    PubMed  CAS  Google Scholar 

  78. Lederer, M. (1990) Adsorption chromatography on cellulose. VI. Further studies on the separation of D-and L-tryptophan on cellulose with aqueous solvents. J. Chromatogr. 510, 367–371.

    CAS  Google Scholar 

  79. Shimada, A., Fukuhara, T., Isoyama, M., Itoh, M., and Yuasa, S. (1989) Construction of chiral evolution model. Viva Origino 17, 53–62.

    CAS  Google Scholar 

  80. Shimada, A., Fukuhara, T., Isoyama, M., Itoh, M., and Yuasa, S. (1990) Construction of chiral evolution model. Chromatographic resolution of amino acid racemates by use of cellulose. Nagasaki Daigaku Kyoikugakubu Shizen Kagaka Hokoku 42, 53–62.

    Google Scholar 

  81. Lederer, M. (1992) Adsorption chromatography on cellulose. VII. Chiral separation on cellulose with aqueous solvents. J. Chromatogr. 604, 55–62.

    CAS  Google Scholar 

  82. Xuan, H. T. K., Kuhn, A. O., and Lederer, M. (1992) Adsorption chromatography on cellulose. VIII. The salting-out behaviour of some peptides with aromatic groups. J. Chromatogr. 626, 301–304.

    Google Scholar 

  83. Xuan, H. T. K. and Lederer, M. (1993) Adsorption chromatography on cellulose. IX. Chiral separations with aqueous solvents and liquid-liquid systems. J. Chromatogr. 635, 346–348.

    CAS  Google Scholar 

  84. Xuan, H. T. K. and Lederer, M. (1993) Adsorption chromatography on cellulose. X. Adsorption of tryptophan and derivatives from CuSO4-containing eluents. J. Chromatogr. 645, 185–188.

    Google Scholar 

  85. Xuan, H. T. K. and Lederer, M. (1994) Adsorption chromatography on cellulose. XI. Chiral separations with aqueous solutions of cyclodextrins as eluents. J. Chromatogr. 659, 191–197.

    CAS  Google Scholar 

  86. Suedee, R. and Heard, C. M. (1997) Direct resolution of propranolol and bupranolol by thin-layer chromatography using cellulose derivatives as stationary phase. Chirality 9, 139–144.

    CAS  Google Scholar 

  87. Kubota, T., Yamamoto, C., and Okamoto, Y. (2000) Tris(cyclohexylcarbamate)s of cellulose and amylose as potential chiral stationary phases for high-performance liquid chromatography and thin-layer chromatography. J. Am. Chem. Soc. 122, 4056–4059.

    CAS  Google Scholar 

  88. Hesse, G. and Hagel, R. (1976) Über Inclusionschromatographie und ein neues Retentionsprinzip für Benzolderivate. Chromatographia 9, 62–68.

    CAS  Google Scholar 

  89. Hesse, G. and Hagel, R. (1973) Vollständige Racemattrennung durch Elutionschromatographie an Cellulose-tri-acetat. Chromatographia 6, 277–280.

    CAS  Google Scholar 

  90. Faupel, M. (1987) A new microcristalline triacetylcellulose thin-layer plate permitting separation of enantiomers. Separation of racemic oxindanac into its enantiomeric components. 4th Int. Symp. Instrumental TLC, Selvino/Bergamo, Italy.

    Google Scholar 

  91. Günther, K. and Zeller, M. Degussa AG, Hanau, Germany.

    Google Scholar 

  92. Günther, K. and Merget, S. Degussa AG, Hanau, Germany.

    Google Scholar 

  93. Lepri, L., Coas, V., Desideri, P. G., and Zocchi, A. (1994) Reversed phase planar chromatography of enantiomeric compounds on triacetylcellulose. J. Planar Chromatogr. 7, 376–381.

    CAS  Google Scholar 

  94. Lepri, L. (1995) Reversed phase planar chromatography of enantiomeric compounds on microcristalline triacetylcellulose. J. Planar Chromatogr. 8, 467–469.

    CAS  Google Scholar 

  95. Huang, M. B., Sun, J., Wang, J. S., et al. (1997) Separation of pharmaceutical enantiomers on column and thin-layer plate of cellulose triacetate. Acta Pharm. Sinica 32, 612–616.

    CAS  Google Scholar 

  96. Lepri, L., Del Bubba, M., and Masi, F. (1997) Reversed-phase planar chromatography of enantiomeric compounds on microcristalline cellulose triacetate (MCTA). J. Planar Chromatogr. 10, 108–113.

    CAS  Google Scholar 

  97. Lepri, L., Del Bubba, M., Coas, V., and Cincinelli, A. (1999) Reversed-phase planar chromatography of racemic flavanones. J. Liq. Chrom. Rel. Technol. 22, 105–118.

    CAS  Google Scholar 

  98. Lepri, L., Cincinelli, A., and Del Bubba, M. (1999) Reversed-phase planar chromatography of optical isomers on microcristalline cellulose triacetate. J. Planar Chromatogr. 12, 298–301.

    CAS  Google Scholar 

  99. Lepri, L., Del Bubba, M., Cincinelli, A., and Boddi, L. (2000) Inclusion planar chromatography of enantiomeric and racemic compounds. J. Planar Chromatogr. 13, 384–387.

    CAS  Google Scholar 

  100. Lepri, L., Del Bubba, M., Cincinelli, A., and Boddi, L. (2001) Direct resolution of aromatic alcohols by planar chromatography on tribenzoylcellulose as chiral stationary phase. J. Planar Chromatogr. 14, 134–136.

    CAS  Google Scholar 

  101. Alak, A. and Armstrong, D. W. (1986) Thin-layer chromatographic separation of optical, geometrical, and structural isomers. Anal. Chem. 58, 582–584.

    CAS  Google Scholar 

  102. Ward, T. J. and Armstrong, D. W. (1986) Improved cyclodextrin chiral phases: a comparison and review. J. Liq. Chromatogr. 9, 407–423.

    CAS  Google Scholar 

  103. Han, S. M. and Armstrong, D. W. (1990) Enantiomeric separation by thin-layer chromatography. Chem. Anal. 108, 81–100.

    CAS  Google Scholar 

  104. Duncan, J. D. and Armstrong, D. W. (1990) Chiral mobile phase additives in reversed-phase TLC. J. Planar Chromatogr. 3, 65–67.

    CAS  Google Scholar 

  105. Wilson, I. D. (1986) Towards chiral TLC plates: some preliminary studies. Method. Surv. Biochem. Anal. 16, 277–281.

    CAS  Google Scholar 

  106. Bhushan, R. and Martens, J. (1997) Direct resolution of enantiomers by impregnated TLC. Biomed. Chromatogr. 11, 280–285.

    PubMed  CAS  Google Scholar 

  107. Armstrong, D. W., He, F. Y., and Han, S. M. (1988) Planar chromatographic separation of enantiomers and diastereomers with cyclodextrin mobile phase additives. J. Chromatogr. 448, 345–354.

    PubMed  CAS  Google Scholar 

  108. Armstrong, D. W., Faulkner, J. R., Jr., and Han, S. M. (1988) Use of hydroxypropyl-and hydroxyethyl-derivatized β-cyclodextrins for the thin-layer chromatographic separation of enantiomers and diastereomers. J. Chromatogr. 452, 323–330.

    PubMed  CAS  Google Scholar 

  109. Duncan, J. D. and Armstrong, D. W. (1991) A study of the effects of the degree of substitution of hydroxypropyl-β-cyclodextrin used as a chiral mobile phase additive in TLC. J. Planar Chromatogr. 4, 204–206.

    CAS  Google Scholar 

  110. Lepri, L., Coas, V., Desideri, P. G., and Checchini, L. (1990) Separation of optical and structural isomers by planar chromatography with development by β-cyclodextrin solutions. J. Planar Chromatogr. 3, 311–316.

    CAS  Google Scholar 

  111. Lepri, L., Coas, V., Desideri, P. G., et al. (1990) Planar chromatography of isomers using β-cyclodextrin solutions as mobile phase. J. Planar Chromatogr. 3, 533–535.

    CAS  Google Scholar 

  112. Lepri, L., Coas, V., and Desideri, P. G. (1991) Reversed-phase planar chromatography of isomers using α-and β-cyclodextrin solutions as eluents. J. Planar Chromatogr. 4, 338–340.

    CAS  Google Scholar 

  113. Lepri, L., Coas, V., and Desideri, P. G. (1994) Planar chromatography of optical and structural isomers with eluents containing modified β-cyclodextrins. J. Planar Chromatogr. 7, 322–326.

    CAS  Google Scholar 

  114. Xuan, H. T. K. and Leipzig-Pagani, E. (1996) Quantitative thin layer chromatography on cellulose. II. Selected applications: lower alkohols, tryptophan enantiomers, gold and platinum. J. Chromatogr. A 746, 261–268.

    Google Scholar 

  115. Huang, M. B., Li, H. K., Li, G. L., Yan, C. T., and Wang, L. P. (1996) Planar chromatographic direct separation of some aromatic amino acids and aromatic amino amino alcohols into enantiomers using cyclodextrin mobile phase additives. J. Chromatogr. A 742, 289–294.

    CAS  Google Scholar 

  116. LeFevre, J. W. (1993) Reversed-phase thin-layer chromatographic separations of enantiomers of dansyl-amino acids using β-cyclodextrin as a mobile phase additive. J. Chromatogr. 653, 293–302.

    CAS  Google Scholar 

  117. Hao, A. Y., Tong, L. H., Zhang, F. S., and Gao, X. M., and Inoue, Y. (1995) Direct thin-layer chromatographic separations of enantiomers of six selected amino acids using 2-O-[(R)-2-hydroxypropyl]-β-CD as a mobile phase additive. Anal. Lett. 28, 2041–2048.

    CAS  Google Scholar 

  118. Lambroussi, V., Piperaki, S., and Tsantili-Kakoulidou, A. (1999) Formation of inclusion-complexes between cyclodextrins, as mobile phase additives in RPTLC, and fluoxetine, norfluoxetine, and promethazine. J. Planar Chromatogr. 12, 124–128.

    CAS  Google Scholar 

  119. Aboul-Enein, H. Y., El-Awady, M. I., and Heard, C. M. (2000) Enantiomeric separation of aminoglutethimide, acetyl aminoglutethimide, and dansyl aminoglutethimide by TLC with β-cyclodextrin and derivatives as mobile phase additives. J. Liq. Chrom. Rel. Technol. 23, 2715–2726.

    CAS  Google Scholar 

  120. LeFevre, J. W., Gublo, E. J., Botting, C, et al. (2000) Qualitative reversed-phase thin-layer chromatographic analysis of the stereochemistry of D-and L-α-amino acids in small peptides. J. Planar Chromatogr. 13, 160–165.

    CAS  Google Scholar 

  121. LeFevre, J. W., Rogers, E. D., Pico, L. L., and Botting, C. L. (2000) The effect of structure on the resolution of dansyl amino acids using beta-cyclodextrin as a mobile phase additive in reversed-phase thin-layer chromatography. Chromatographia 52, 648–652.

    CAS  Google Scholar 

  122. Bhushan, R. and Parshad, V. (1996) Resolution of (±)-ibuprofen using L-arginine-impregnated thin-layer chromatography. J. Chromatogr. A 721, 369–372.

    CAS  Google Scholar 

  123. Bhushan, R. and Thiongo, G. T. (1998) Direct enantioseparation of some β-adrenergetic blocking agents using impregnated thin-layer chromatography. J. Chromatogr. B 708, 330–334.

    CAS  Google Scholar 

  124. Bhushan, R. and Thiongo, G. T. (1999) Direct enantiomeric resolution of some 2-arylpropionic acids using (−)-brucine-impregnated thin-layer chromatography. Biomed. Chromatogr. 13, 276–278.

    PubMed  CAS  Google Scholar 

  125. Huang, M. B., Li, G. L., Yang, G. S., Shi, Y. H., Gao, J. J., and Liu, X. D. (1997) Enantiomeric separation of aromatic amino alkohol drugs by chiral ion-pair chromatography on a silica gel plate. J. Liq. Chrom. Rel. Technol. 20, 1507–1514.

    CAS  Google Scholar 

  126. Li, G., Huang, M., Yang, G., Wu, G., and Du, A. (1999) The enantiomeric separation of aromatic amino alkohol drugs by thin-layer chromatography. Chin. J. Chromatogr. 17, 215–216.

    CAS  Google Scholar 

  127. Deng, Q., Kang, S., Zhu, Q., and Xu, Z. (1999) Study of a new cyclodextrin bonded stationary phase for thin-layer chromatographic chiral separations. Am. Lab. 31, 43–47.

    CAS  Google Scholar 

  128. Zhu, Q., Ma, G., Deng, Q., and Zeng, L. (2000) Preparation and application of phenylcarbamate-substituted β-cyclodextrin bonded stationary phase used for thin-layer chromatography. Chin. J. Anal. Chem. 28, 349–352.

    CAS  Google Scholar 

  129. Zhu, Q., Yu, P., Deng, Q., and Zeng, L. (2001) β-Cyclodextrin-bonded chiral stationary phase for thin-layer chromatographic separation of enantiomers. J. Planar Chromatogr. 14, 137–139.

    CAS  Google Scholar 

  130. Paris, R. R., Sarsunova, M., and Semonsky, M. (1967) La chromatographie en couche mince comme mäthode de dädoublement des alcaloides racämiques. Application aux mädicaments contenant de ľäphädrine. Ann. Pharm. Franc. 25, 177–180.

    PubMed  CAS  Google Scholar 

  131. Wainer, I. W., Brunner, C. A., and Doyle, T. D. (1983) Direct resolution of enantiomers via thin-layer chromatography using a chiral adsorbent. J. Chromatogr. 264, 154.

    CAS  Google Scholar 

  132. Oi, N. (1985) Direct separation of optically active isomers by chromatographic methods. Farumashia, 21, 747–752.

    CAS  Google Scholar 

  133. Bhushan, R. and Ali, I. (1987) Resolution of enantiomeric mixtures of phenylthiohydantoin amino acids on (+)-tartaric acid-impregnated silica gel plates. J. Chromatogr. 392, 460–463.

    PubMed  CAS  Google Scholar 

  134. Bhushan, R. and Ali, I. (1987) TLC Resolution of enantiomeric mixtures of amino acids. Chromatographia 23, 141–142.

    CAS  Google Scholar 

  135. Wall, P. E. (1989) Proceedings of the International Symposium on Instrumental Thin Layer Chromatography/Planar Chromatography, Brighton, Sussex, U.K.

    Google Scholar 

  136. Wall, P. E. (1989) Preparation and Application of HPTLC plates for enantiomer separation. J. Planar Chromatogr. 2, 228–232.

    CAS  Google Scholar 

  137. Brunner, C. A. and Wainer, I. (1989) Direct stereochemical resolution of enantiomeric amides via thin-layer chromatography on a covalently bonded chiral stationary phase. J. Chromatogr. 472, 277–283.

    PubMed  CAS  Google Scholar 

  138. Tivert, A. M. and Backman, A. (1989) Enantiomeric separation of aminoalcohols by TLC using chiral counter-ion in the mobile phase. J. Planar Chromatogr. 2, 472–473.

    CAS  Google Scholar 

  139. Duncan, J. D. (1990) Chiral separations: a comparison of HPLC and TLC. J. Liq. Chromatogr. 13, 2737–2755.

    CAS  Google Scholar 

  140. Duncan, J. D., Armstrong, D. W., and Stalcup, A. M. (1990) Normal phase TLC separation of enantiomers using chiral ion interaction agents. J. Liq. Chromatogr. 13, 1091–1103.

    CAS  Google Scholar 

  141. Brand, K., Kinkel, J., and Nagel, J. (1988) Chromatographieplatten und Verfahren zur dünnschicht-chromatographischen Trennung von Enantiomeren. DE 3843266, Merck Patent GmbH, Darmstadt, Germany.

    Google Scholar 

  142. Witherow, L., Spurway, T. D., Ruane, R. J., Wilson, I. D., and Longdon, K. (1991) Problems and solutions in chiral thin-layer chromatography: a two-phase “Pirkle” modified amino-bonded plate. J. Chromatogr. 553, 497–501.

    CAS  Google Scholar 

  143. Lohmann, D. and Däppen, R. (1991) Enantiomeric silanes, modified packing materials, and use thereof. U.S. Patent 4,997,965.

    Google Scholar 

  144. Lepri, L., Coas, V., and Desideri, P. G. (1992) Planar chromatography of optical isomers with bovine serum albumin in the mobile phase. J. Planar Chromatogr. 5, 175–178.

    CAS  Google Scholar 

  145. Lepri, L., Coas, V., and Desideri, P. G. (1992) Reversed phase planar chromatography of optically active fluorenylmethoxycarbonyl amino acids with bovine serum albumin in the mobile phase. J. Planar Chromatogr. 5, 294–296.

    CAS  Google Scholar 

  146. Lepri, L., Coas, V., Desideri, P. G., and Zocchi, A. (1992) Reversed phase planar chromatography of enantiomeric tryptophans with bovine serum albumin in the mobile phase. J. Planar Chromatogr. 5, 234–238.

    CAS  Google Scholar 

  147. Lepri, L., Coas, V., Desideri, P. G., and Pettini, L. (1992) Reversed phase planar chromatography of enantiomeric compounds with bovine serum albumin in the mobile phase. J. Planar Chromatogr. 5, 364–367.

    CAS  Google Scholar 

  148. Lepri, L., Coas, V., Desideri, P. G., and Santianni, D. (1993) Reversed phase planar chromatography of dansyl DL amino acids with bovine serum albumin in the mobile phase. Chromatographia 36, 297–301.

    CAS  Google Scholar 

  149. Lepri, L., Coas, V., Desideri, P. G., and Pettini, L. (1993) Thin layer chromatographic enantioseparation of miscellaneous compounds with bovine serum albumin in the eluent. J. Planar Chromatogr. 6, 100–104.

    CAS  Google Scholar 

  150. Lepri, L., Coas, V., Desideri, P. G., and Zocchi, A. (1994) The mechanism of retention of enantiomeric solutes on silanized silica plates eluted with albumin solutions. J. Planar Chromatogr. 7, 103–107.

    CAS  Google Scholar 

  151. Tivert, A. M. and Backman, A. (1993) Separation of the enantiomers of β-blocking drugs with a chiral mobile phase additive. J. Planar Chromatogr. 6, 216–219.

    CAS  Google Scholar 

  152. Bhushan, R. and Ali, I. (1993) Resolution of racemic mixtures of hyoscyamine and colchicine on impregnated silica gel layers. Chromatographia 35, 679–680.

    CAS  Google Scholar 

  153. Armstrong, D. W. and Zhou, Y. (1994) Use of macrocyclic antibiotic as the chiral selector for enantiomeric separations by TLC. J. Liq. Chromatogr. 17, 1695–1707.

    CAS  Google Scholar 

  154. Bhushan, R. and Thiongo, G. T. (2000) Separation of the enantiomers of dansyl-D,L-amino acids by normal-phase TLC on plates impregnated with a macrocyclic antibiotic. J. Planar Chromatogr. 13, 33–36.

    CAS  Google Scholar 

  155. Bhushan, R. and Parshad, V. (1996) Thin-layer chromatographic separation of enantiomeric dansylamino acids using a macrocyclic antibiotic as a chiral selector. J. Chromatogr. A 736, 235–238.

    CAS  Google Scholar 

  156. Lindner, W. (1981) Trennung von Enantiomeren mittels moderner Flüssigkeits-Chromatographie. Chimia 35, 294–307.

    CAS  Google Scholar 

  157. Davankov, V. A., Bochkov, A. S., Kurganov, A. A., Roumeliotis, P., and Unger, K. K. (1980) Separation of unmodified α-amino acid enantiomers by reversed phase HPLC. Chromatographia 13, 677–685.

    CAS  Google Scholar 

  158. Kurganov, A. A., Ponomaryova, T. M., and Davankov, V. A. (1984) Copper(II) complexes with optically active diamines. V. Enantioselective effects in equally-paired and mixed-ligand copper(II) complexes with diamines. Inorg. Chim. Acta 86, 145–149.

    CAS  Google Scholar 

  159. Günther, K., Martens, J., and Schickedanz, M. (1984) Dünnschichtchromatographische Enantiomerentrennung mittels Ligandenaustausch. Angew. Chem. 96, 514–515; (1984) Thin-layer chromatographic enantiomeric resolution via ligand exchange. Angew. Chem. Int. Ed. Engl. 23, 506.

    Google Scholar 

  160. Weinstein, S. (1984) Resolution of optical isomers by thin layer chromatography. Tetrahedron Lett. 25, 985–986.

    CAS  Google Scholar 

  161. Grinberg, N. and Weinstein, S. (1984) Enantiomeric separation of Dns-amino acids by reversed-phase thin-layer chromatography. J. Chromatogr. 303, 251–255.

    CAS  Google Scholar 

  162. Grinberg, N. (1985) Thin-layer chromatographic separation using a temperature gradient. J. Chromatogr. 333, 69–81.

    CAS  Google Scholar 

  163. Marchelli, R., Virgili, R., Armani, E., and Dossena, A. (1986) Enantiomeric separation of D,L-Dns-amino acids by one-and two-dimensional thin-layer chromatography. J. Chromatogr. 355, 354–357.

    CAS  Google Scholar 

  164. Davankov, V. A., Bochkov, A. S., and Belov, Y. P. (1981) Ligand exchange chromatography of racemates. XV. Resolution of α-amino acids on reversed-phase silica gels coated with N-decyl-L-histidine. J. Chromatogr. 218, 547–557.

    CAS  Google Scholar 

  165. Martens, J., Weigel, H., Busker, E., and Steigerwald, R. (1987) Optisch aktive Prolin-Derivate, Verfahren zur ihrer Herstellung und ihre Verwendung. DE-PS 3143726, Degussa AG, Hanau, Germany.

    Google Scholar 

  166. Lübben, S., Martens, J., Haase, D., Pohl, S., and Saak, W. (1990) Dünnschichtchromatographische Enantiomerentrennung nach dem Ligandenaustauschprinzip: Synthese und Struktur eines chiralen Modellkomplexes. Tetrahedron Lett. 31, 7127–7128.

    Google Scholar 

  167. Martens, J. and Lubben, S. (1990) Synthese sterisch einheitlicher Selektoren zur dünnschichtchromatographischen Racematspaltung nach dem Ligandenaustauschprinzip. Tetrahedron 46, 1231–1234.

    CAS  Google Scholar 

  168. Bhushan, R., Reddy, G. P., and Joshi, S. (1994) TLC resolution of DL amino acids on impregnated silica gel plates. J. Planar Chromatogr. 7, 126–128.

    CAS  Google Scholar 

  169. Günther, K. and Rausch, R. (1985) Thin-layer chromatographic enantiomeric resolution based on ligand exchange. Proc. 3rd Int. Symp. Instrumental HPTLC, Würzburg, FRG; Inst. Chromatogr. Bad Dürkheim, pp. 469–475.

    Google Scholar 

  170. Günther, K. (1988) Thin-layer chromatographic enantiomeric resolution via ligand exchange. J. Chromatogr. 448, 11–30.

    PubMed  Google Scholar 

  171. Brinkman, U. A. T. and Kamminga, D. (1985) Rapid separation of enantiomers by thin-layer chromatography on a chiral stationary phase. J. Chromatogr. 330, 375–378.

    CAS  Google Scholar 

  172. Jork, H. and Kany, E. (1986) GDCh-Fortbildungskurs, No. 301, Saarbrücken, Germany.

    Google Scholar 

  173. Brückner, H., Bosch, I., Graser, T., and Fürst, P. (1987) Determination of α-alkyl-α-amino acids and α-amino alkohols by chiral-phase capillary gas chromatography and reversed-phase high-performance liquid chromatography. J. Chromatogr. 395, 569–590.

    PubMed  Google Scholar 

  174. Brückner, H. (1987) Enantiomeric resolution of N-methyl-α-amino acids and α-alkyl-α-amino acids by ligand-exchange chromatography. Chromatographia 24, 725–738.

    Google Scholar 

  175. Gont, L. K. and Neuendorf, S. K. (1987) Enantiomeric separation of N-carbamyltryptophan by thin-layer chromatography on a chiral stationary phase. J. Chromatogr. 391, 343–345.

    PubMed  CAS  Google Scholar 

  176. Kovács-Hadady, K. and Kiss, I. T. (1987) Attempts for the chromatographic separation of D-and L-penicillamine enantiomers. Chromatographia 24, 677–679.

    Google Scholar 

  177. Feldberg, R. S. and Reppucci, L. M. (1987) Rapid separation of anomeric purine nucleosides by thin-layer chromatography on a chiral stationary phase. J. Chromatogr. 410, 226–229.

    PubMed  CAS  Google Scholar 

  178. Detolle, S., Postaire, E., Gimenez, F., Prognon, P., and Pradeau, D. (1988) Thin layer chromatography and liquid chromatography of thiorphan enantiomers and their diastereoisomers degradation products. 1st Int. Symp. Separation of Chiral Molecules, May 31–June 2, Paris, France.

    Google Scholar 

  179. Mack, M., Hauck, H. E., and Herbert, H. (1988) Enantiomeric separation in TLC with the new HPTLC pre-coated plate CHIR with concentrating zone. J. Planar Chromatogr. 1, 304–308.

    CAS  Google Scholar 

  180. Mack, M., Hauck, H. E., and Jost, W. (1988) HPTLC pre-coated plate CHIR with concentrating zone. A new layer for separation of enantiomers. 17th Int. Symp. Chromatography, September 25–30, Wien, Austria.

    Google Scholar 

  181. Schlauch, M. (2001) Chirale Analytik von aliphatischen und cycloaliphatischen Aminosäuren mit chromatographischen und elektrophoretischen Methoden. (Thesis, Frahm, A. W.) Albert-Ludwig Universität Freiburg.

    Google Scholar 

  182. Bhushan, R., Mahesh, V. K., and Mallikharjun, P. V. (1989) Thin layer chromatography of peptides and proteins: a review. Biomed. Chromatogr. 3, 95–104.

    PubMed  CAS  Google Scholar 

  183. Zydowsky, T. M., de Lara, E., and Spanton, S. G. (1990) Stereoselective synthesis of α-alkyl α-amino acids. Alkylation of 3-substituted 5H,10bH-oxazolo[3,2-c][1,3]benzoxazine-2(3H),5-diones. J. Org. Chem. 55, 5437–5439.

    CAS  Google Scholar 

  184. Toth, G., Lebl, M., and Hruby, V. J. (1990) Chiral thin-layer chromatographic separation of phenylalanine and tyrosine derivatives. J. Chromatogr. 504, 450–455.

    CAS  Google Scholar 

  185. Euerby, M. R. (1990) Resolution of the neuroexcitatory N-methylaspartic acid (2-methylaminosuccinic acid) enantiomers by ligand exchange thin layer chromatography. J. Chromatogr. 502, 226–229.

    PubMed  CAS  Google Scholar 

  186. Hauck, H. E. and Mack, M. (1990) Precoated plates with concentrating zones: a convenient tool for thin-layer chromatography. LC-GC, 8, 88–96.

    CAS  Google Scholar 

  187. Lin, S.-L., Chen, S.-T., Wu, S.-H., and Wang, K. T. (1991) Separation of aspartame and its precursor stereoisomers by chiral chromatography. J. Chromatogr. 540, 392–396.

    CAS  Google Scholar 

  188. Marseigne, I. (1991) Direct separation of enantiomers of amino acids and dipeptides by TLC and HPLC. Second International Symposium on Chiral Discrimination, Roma.

    Google Scholar 

  189. Suzuki, M., Naitho, G., and Takitani, S. (1992) Determination of optical purity of L-amino acids by thin-layer densitometry. lyakuhin Kenkyu 23, 49–52.

    CAS  Google Scholar 

  190. Pyka, A. (1993) A new optical topological index (Iopt) for predicting the separation of D and L optical isomers by TLC Part III. J. Planar Chromatogr. 6, 282–288.

    CAS  Google Scholar 

  191. Aboul-Enein, H. Y. and Serignese, V. (1994) Optical purity of thyroxine enantiomers in bulk materials by chiral thin layer chromatography. 5th International Symposium on Chiral Discrimination, Stockholm.

    Google Scholar 

  192. Nyiredy, Sz., Dallenbach-Toelke, K., Günther, K., and Sticher, O. (1988) Applicability of forced-flow planarchromatographic methods for the separation of chiral molecules. 1st Int. Symp. Separation of Chiral Molecules, May 31–June 2, Paris, France.

    Google Scholar 

  193. Nyiredy, Sz., Dallenbach-Toelke, K., and Sticher, O. (1988) Applicability of forced-flow planar chromatographic methods for the separation of enantiomers on chiralplate. J. Chromatogr. 450, 241–252.

    CAS  Google Scholar 

  194. Günther, K., Martens, J., and Schickedanz, M. (1985) Thin-layer chromatographic enantiomeric resolution. Naturwissenschaften 72, 149–150.

    Google Scholar 

  195. Günther, K., Martens, J., and Schickedanz, M. (1985) Resolution of optical isomers by thin-layer chromatography (TLC). Enantiomeric Purity of L-DOPA. Z. Anal. Chem. 332, 513–514.

    Google Scholar 

  196. Günther, K., Martens, J., and Schickedanz, M. (1986) Dünnschichtchromatographische Trennung stereoisomerer Dipeptide. Angew. Chem. 98, 284–285; (1986) Thin layer chromatographic separation of stereoisomeric dipeptides. Angew. Chem. Int. Ed. Engl. 25, 278–279.

    Google Scholar 

  197. Günther, K., Martens, J., and Schickedanz, M. (1986) Resolution of optical isomers by thin-layer chromatography: enantiomeric purity of D-penicillamine. Arch. Pharm. (Weinheim Ger.) 319, 461–465.

    Google Scholar 

  198. Martens, J., Günther, K., and Schickedanz, M. (1986) Resolution of optical isomers by thin-layer chromatography: enantiomeric purity of methyldopa. Arch. Pharm. (Weinheim Ger.) 319, 572–574.

    CAS  Google Scholar 

  199. Günther, K., Schickedanz, M., Drauz, K., and Martens, J. (1986) Thin-layer chromatographic enantiomeric resolution of α-alkyl amino acids. Z. Anal. Chem. 325, 298–299.

    Google Scholar 

  200. Günther, K. (1986) Dünnschichtchromatographische Enantiomerentrennung mittels Ligandenaustausch. GIT; Suppl. 3, 6–12.

    Google Scholar 

  201. Klaus, R. and Fischer, W. (1987) A means of analysing glycols, especially ethylene glycol and diethylene glycol, by a method used for the determination of carbohydrates in alcoholic beverages. Chromatographia 23, 137–140.

    CAS  Google Scholar 

  202. Günther, K. and Schickedanz, M. (1987) Quantitative Auswertung von dc-getrennten Enantiomeren GIT; Suppl. 3, 27–32.

    Google Scholar 

  203. Günther, K. and Rausch, R. (1987) Quantitative determination of TLC-separated enantiomers of amino acides. 4th Int. Symp. Instrumental TLC, Selvino/Bergamo, Italy.

    Google Scholar 

  204. Günther, K. (1988) Détermination quantitative des énantiomères d’acides aminés par chromatographie sur couche mince (CCM). Analysis 16, 514–518.

    Google Scholar 

  205. Funk, W. and Heiligenthal, M. (1984) Nachbehandlung von DC-Platten durch instrumentalisiertes Tauchen. GIT; Suppl. 4(5), 49–51.

    Google Scholar 

  206. Funk, W., Dammann, V., Vonderheid, C., and Oehlmann, G. (1985) Statistische Methoden in der Wasseranalytik, VCH Weinheim.

    Google Scholar 

  207. Barooshian, A. V., Lautenschleger, M. J., and Harris, W. G. (1972) Thin layer chromatographic separation of optical isomers of labeled DOPA via dipeptide formation. Anal. Biochem. 49, 569–571.

    PubMed  CAS  Google Scholar 

  208. Eskes, D. (1976) A procedure for the differentiation of the optical isomers of amphetamine and methamphetamine by thin-layer chromatography. J. Chromatogr. 117, 442–444.

    PubMed  CAS  Google Scholar 

  209. Kolodziejczyk, A. M. and Arendt, A. (1979) Use of tritium labelled compounds in peptide chemistry. Determination of enantiomeric purity of amino acid derivatives by the radiochromatographic method. Polish J. Chem. 53, 1017–1023.

    CAS  Google Scholar 

  210. Jarman, M. and Stec, W. J. (1979) Formation of diastereomeric derivatives from the enantiomers of the antitumour agent cyclophosphamide by reaction with 1-phenethyl alcohol, and their separation by thin-layer chromatography. J. Chromatogr. 176, 440–443.

    CAS  Google Scholar 

  211. Gübitz, G. and Mihellyes, S. (1984) Optical resolution of β-blocking agents by thin-layer chromatography and high-performance liquid chromatography as diastereomeric R-(−)-1-(1-naphthyl)ethylureas. J. Chromatogr. 314, 462–466.

    PubMed  Google Scholar 

  212. Weber, H., Spahn, H., Mutschler, E., and Möhrke, W. (1984) Activated α-alkyl-α-arylacetic acid enantiomers for stereoselective thin-layer chromatographic and high-performance liquid chromatographic determination of chiral amines. J. Chromatogr. 307, 145–153.

    PubMed  CAS  Google Scholar 

  213. Rossetti, V., Lombard, A., and Buffa, M. (1986) The HPTLC resolution of the enantiomers of some 2-arylpropionic acid anti-inflammatory drugs. J. Pharm. Biomed. Anal. 4, 673–676.

    PubMed  CAS  Google Scholar 

  214. Beneytout, J. L., Tixier, M., and Rigaud, M. (1986) Capillary gas-liquid or thin-layer chromatographic resolution of 2-hydroxy-fatty acid enantiomers. J. Chromatogr. 351, 363–365.

    CAS  Google Scholar 

  215. Slégel, P., Vereczkey-Donáth, G., Ladányi, L., and Tóth-Lauritz, M. (1987) Enantiomeric separation of chiral carboxylic acids, as their diastereomeric carboxamides, by thin layer chromatography. J. Pharm. Biomed. Anal. 5, 665–673.

    PubMed  Google Scholar 

  216. Ruterbories, K. J. and Nurok, D. (1987) Thin-layer chromatographic separation of diastereomeric amino acid derivatives prepared with Marfey’s reagent. Anal. Chem. 59, 2735–2736.

    CAS  Google Scholar 

  217. Comber, R. N. and Brouillette, W. J. (1987) Resolution of carnitine an 4-methylcarnitine via the esters formed with (S)-(+)-methoxyphenylacetic acid. J. Org. Chem. 52, 2311–2314.

    CAS  Google Scholar 

  218. Pflugmann, G., Spahn, H., and Mutschler, E. (1987) Rapid determination of the enantiomers of metoprolol, oxprenolol and propranolol in urine. J. Chromatogr. 416, 331–339.

    PubMed  CAS  Google Scholar 

  219. Büyüktimkin, N. and Buschauer, A. (1988) Separation and determination of some amino acid ester enantiomers by thin-layer chromatography after derivatisation with (S)-(+)-naproxen. J. Chromatogr. 450, 281–283.

    PubMed  Google Scholar 

  220. Spell, J. C. and Stewart, J. T. (1997) A high-performance thin-layer chromatographic assay of pindolol enantiomers by chemical derivatization. J. Planar Chromatogr. 10, 222–224.

    CAS  Google Scholar 

  221. Nagata, Y., Iida, T., and Sakai, M. (2001) Enantiomeric resolution of amino acids by thin-layer chromatography. J. Mol. Catal. B Enzym. 12, 105–108.

    CAS  Google Scholar 

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Günther, K., Richter, P., Möller, K. (2004). Separation of Enantiomers by Thin-Layer Chromatography. In: Gübitz, G., Schmid, M.G. (eds) Chiral Separations. Methods in Molecular Biology, vol 243. Humana Press. https://doi.org/10.1385/1-59259-648-7:029

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