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Chromatographia

, Volume 75, Issue 15–16, pp 815–838 | Cite as

Chiral Recognition Mechanisms in Analytical Separation Sciences

  • Gerhard K. E. ScribaEmail author
Review

Abstract

Chiral recognition phenomena play an important role in nature as well as analytical separation sciences. In chromatography and capillary electrophoresis, enantiospecific interactions between a chiral selector and the enantiomers of an analyte resulting in transient diastereomeric complexes are required in order to achieve enantioseparations. The formation of the complexes is driven by ionic interactions, ion–dipole or dipole–dipole interactions, H-bonds, van der Waals interactions and π–π interactions. Due to the structural variety of chiral selectors applied in separation sciences, different mechanisms and structural features contribute to the chiral recognition processes. Besides structure–separation relationship studies in HPLC and CE spectroscopic techniques including NMR spectroscopy, circular dichroism and vibrational circular dichroism spectroscopy as well as molecular modeling methods have significantly contributed to the understanding of the enantiospecific recognition of enantiomers by chiral selectors. The present review briefly illustrates the current models of the enantiospecific recognition on a structural basis of various chiral selectors including polysaccharide derivatives, cyclodextrins, cyclofructan derivatives, macrocyclic glycopeptides, proteins, Pirkle-type selectors, ion exchangers, polymers, crown ethers, ligand exchangers, calixarenes, aptamers, micelles forming agents and ionic liquids.

Keywords

Enantiomer separation Chiral separation Chrial selector Chiral recognition mechanism Complex formation 

References

  1. 1.
    Chankvetadze B (1997) J Chromatogr A 792:269–295CrossRefGoogle Scholar
  2. 2.
    Chankvetadze B, Schulte G, Blaschke G (1997) Enantiomer 2:157–179Google Scholar
  3. 3.
    Chankvetadze B (2002) Electrophoresis 23:4022–4035CrossRefGoogle Scholar
  4. 4.
    Hammitzsch-Wiedemann M, Scriba GKE (2009) Anal Chem 81:8765–8773CrossRefGoogle Scholar
  5. 5.
    Hammitzsch-Wiedemann M, Scriba GKE (2010) Anal Chem 82:6744CrossRefGoogle Scholar
  6. 6.
    Chankvetadze B, Linder W, Scriba GKE (2004) Anal Chem 76:4256–4260CrossRefGoogle Scholar
  7. 7.
    Ali KK, Aboul-Enein HY (2006) Chromatographia 63:295–307CrossRefGoogle Scholar
  8. 8.
    Berthod A (2006) Anal Chem 78:2093–2099CrossRefGoogle Scholar
  9. 9.
    Lämmerhofer M (2010) J Chromatogr A 1217:814–856CrossRefGoogle Scholar
  10. 10.
    Berthod A (2010) Chiral recognition in separation methods. Springer, HeidelbergCrossRefGoogle Scholar
  11. 11.
    Beesley T, Majors RE (2011) LCGC North Am 28:642–651Google Scholar
  12. 12.
    Schurig V (2010) Ann Pharm Franc 68:82–98Google Scholar
  13. 13.
    Cavazzini A, Pasti L, Massi A, Marchetti N, Dondi F (2011) Anal Chim Acta 706:205–222CrossRefGoogle Scholar
  14. 14.
    Chandrul KK, Srivastava B (2010) J Chem Pharm Res 2:923–934Google Scholar
  15. 15.
    Zhang Y, Yao S, Zeng H, Song H (2010) Curr Pharm Anal 6:114–130CrossRefGoogle Scholar
  16. 16.
    Chankvetadze B (2007) J Chromatogr A 1168:45–70CrossRefGoogle Scholar
  17. 17.
    Gübitz G, Schmid MG (2008) J Chromatogr A 1204:140–156CrossRefGoogle Scholar
  18. 18.
    Preinstorfer B, Lämmerhofer M, Lindner W (2009) Electrophoresis 30:100–132CrossRefGoogle Scholar
  19. 19.
    Scriba GKE (2011) J Pharm Biomed Anal 55:688–701CrossRefGoogle Scholar
  20. 20.
    Scriba GKE (2011) Bioanal Rev 3:95–114CrossRefGoogle Scholar
  21. 21.
    Ward TJ, Ward KD (2010) Anal Chem 82:4712–4722CrossRefGoogle Scholar
  22. 22.
    Ward TJ, Ward KD (2012) Anal Chem 84:626–635CrossRefGoogle Scholar
  23. 23.
    Easson LH, Stedman E (1933) Biochem J 27:1257–1266Google Scholar
  24. 24.
    Danakov VA (1997) Chirality 9:99–102CrossRefGoogle Scholar
  25. 25.
    Topiol S (1989) Chirality 1:69–79CrossRefGoogle Scholar
  26. 26.
    Dodziuk H, Kozinski W, Ejchart A (2004) Chirality 16:90–105CrossRefGoogle Scholar
  27. 27.
    Uccello-Barretta G, Vanni L, Balzano F (2010) J Chromatogr A 1217:928–940CrossRefGoogle Scholar
  28. 28.
    Morris KF, Froberg AL, Becker BA, Almeida VK, Tarus J, Larive CK (2005) Anal Chem 77:254A–263ACrossRefGoogle Scholar
  29. 29.
    Lipkowitz KB (2001) Atomistic modeling of enantioselection in chromatography. J Chromatogr A 906:417–442CrossRefGoogle Scholar
  30. 30.
    Del Rio A (2009) J Sep Sci 32:1566–1584CrossRefGoogle Scholar
  31. 31.
    Hesse G, Hagel R (1973) Chromatographia 6:277–280CrossRefGoogle Scholar
  32. 32.
    Okamoto Y, Kawashima M, Hatada K (1986) J Chromatogr 363:173–186CrossRefGoogle Scholar
  33. 33.
    Okamoto Y, Aburatani R, Fukumoto T, Hatada K (1987) Chem Lett 16:1857–1860CrossRefGoogle Scholar
  34. 34.
    Chen X, Yamamoto C, Okamoto Y (2007) Pure Appl Chem 79:1561–1573CrossRefGoogle Scholar
  35. 35.
    Okamoto Y, Ikai T (2008) Chem Soc Rev 37:2593–2608CrossRefGoogle Scholar
  36. 36.
    Ikai T, Yamamoto C, Kamigaito M, Okamoto Y (2008) Int J Chromatogr B 875:2–11CrossRefGoogle Scholar
  37. 37.
    Ika T, Okamoto Y (2009) Chem Rev 109:6077–6101CrossRefGoogle Scholar
  38. 38.
    Yamamoto C, Yashima E, Okamoto Y (2002) J Am Chem Soc 124:12583–12589CrossRefGoogle Scholar
  39. 39.
    Ye YK, Bai S, Vyas S, Wirth MJ (2007) J Phys Chem B 111:1189–1198CrossRefGoogle Scholar
  40. 40.
    Kasat RB, Wang NHL, Franses EI (2007) Biomacromolecules 8:1676–1685CrossRefGoogle Scholar
  41. 41.
    Kasat RB, Zvinevich Y, Hillhouse HW, Thomson KT, Wang NHL, Franses EI (2006) J Phys Chem B 110:14114–14122CrossRefGoogle Scholar
  42. 42.
    Ma S, Shen S, Lee H, Yee N, Senanayake C, Nafie LA, Grinberg N (2008) Tetrahedron Asymmetry 19:2111–2114CrossRefGoogle Scholar
  43. 43.
    Ma S, Shen S, Lee H, Eriksson M, Zeng X, Xu J, Fandrick K, Yee N, Senanayake C, Grinberg N (2009) J Chromatogr A 1216:3784–3793CrossRefGoogle Scholar
  44. 44.
    Kasat RB, Wee SY, Loh JX, Wang NHL, Franses EI (2008) J Chromatogr B 875:81–92CrossRefGoogle Scholar
  45. 45.
    Kasat RB, Wang NHL, Franses EI (2008) J Chromatogr A 1190:110–119CrossRefGoogle Scholar
  46. 46.
    Kasat RB, Fransies EI, Wang NHL (2010) Chirality 22:565–579Google Scholar
  47. 47.
    Yamamoto C, Yashima E, Okamoto Y (1999) Bull Chem Soc Jpn 72:1815–1825CrossRefGoogle Scholar
  48. 48.
    Wenslow RM, Wang T (2001) Anal Chem 73:4190–4195CrossRefGoogle Scholar
  49. 49.
    Wang T, Wenslow RM (2003) J Chromatogr A 1015:99–110CrossRefGoogle Scholar
  50. 50.
    Okamoto M (2002) J Pharm Biomed Anal 27:401–407CrossRefGoogle Scholar
  51. 51.
    Xiang C, Liu G, Kang S, Guo X, Yao B, Weng W, Zeng Q (2011) J Chromatogr A 1218:8718–8721CrossRefGoogle Scholar
  52. 52.
    Yao B, Liu G, Kang S, Xiang C, Huang B, Weng Wm Zeng Q (2011) Chromatographia 74:625–631CrossRefGoogle Scholar
  53. 53.
    Chankvetadze L, Ghibradze N, Karchkhadze M, Peng L, Farkas T, Chankvetadze B (2011) J Chromatogr A 1218:6554–6560CrossRefGoogle Scholar
  54. 54.
    Dossou KSS, Edorh PA, Chiap P, Chankvetadze B, Servais AC, Fillet M, Crommen J (2011) J Sep Sci 34:1772–1780CrossRefGoogle Scholar
  55. 55.
    West C, Guenegou G, Zhang Y, Morin-Allory L (2011) J Chromatogr A 1218:2033–2057CrossRefGoogle Scholar
  56. 56.
    Tamura K, Sam NSM, Ikai T, Okamoto Y, Yashima E (2011) Bull Chem Soc Jpn 84:741–747CrossRefGoogle Scholar
  57. 57.
    Wei W, Guo B, Lin JM (2009) Electrophoresis 30:1380–1387CrossRefGoogle Scholar
  58. 58.
    Biwer A, Antranikian G, Heinzle E (2002) Appl Microbiol Biotechnol 59:609–617CrossRefGoogle Scholar
  59. 59.
    Rekharsky MV, Inoue Y (1998) Chem Rev 98:1875–1917CrossRefGoogle Scholar
  60. 60.
    Schurig V (2002) Trends Anal Chem 21:647–661CrossRefGoogle Scholar
  61. 61.
    Han SM (1997) Biomed Chromatogr 11:259–271CrossRefGoogle Scholar
  62. 62.
    Mitchell CR, Armstrong DW (2004) In: Gübitz G, Schmid MG (eds) Chiral separations methods and protocols. Methods in moelcular biology, vol 243. Humana Press, Totowa, pp 61–112Google Scholar
  63. 63.
    Muderawan IW, Ong TT, Ng SC (2006) J Sep Sci 29:1849–1871CrossRefGoogle Scholar
  64. 64.
    Fanali S (2000) J Chromatogr A 875:89–122CrossRefGoogle Scholar
  65. 65.
    Schmitt U, Branch SK, Holzgrabe U (2002) J Sep Sci 25:959–974CrossRefGoogle Scholar
  66. 66.
    Scriba GKE (2008) J Sep Sci 31:1991–2011CrossRefGoogle Scholar
  67. 67.
    Scriba GKE, Altria K (2009) LCGC Eur 22:420–430Google Scholar
  68. 68.
    Fanali S (2009) Electrophoresis 30:S203–S210CrossRefGoogle Scholar
  69. 69.
    Chankvetadze B (2009) Electrophoresis 30:S211–S221CrossRefGoogle Scholar
  70. 70.
    Del Valle EMM (2004) Proc Biochem 39:1033–1046CrossRefGoogle Scholar
  71. 71.
    Buschmann HJ, Knittel D, Schollmeyer E (2001) J Incl Phenom Macro 40:169–172CrossRefGoogle Scholar
  72. 72.
    Dodziuk H (ed) (2006) Cyclodextrins and their complexes. Wiley-VCH, WeinheimGoogle Scholar
  73. 73.
    Hazai E, Hazai I, Demko L, Kovacs S, Malik D, Akli P, Hari P, Szeman J, Fenyvesi E, Benes E, Szente L, Bikadi Z (2010) J Comput Aided Mol Des 24:713–717CrossRefGoogle Scholar
  74. 74.
    Chankvetadze B, Burjanadze N, Maynard DM, Bergander K, Bergenthal D, Blaschke G (2002) Electrophoresis 23:3027–3034CrossRefGoogle Scholar
  75. 75.
    Servais AC, Rousseau A, Fillet M, Lomsadze K, Salgado A, Crommen J, Chankvetadze B (2010) Electrophoresis 31:1467–1474CrossRefGoogle Scholar
  76. 76.
    Servais AC, Rouseseau A, Dive G, Frederich M, Crommen J, Filet M (2012) J Chromatogr A 1232:59–64CrossRefGoogle Scholar
  77. 77.
    Schneider HJ, Hacket F, Rüdiger V, Ikeda H (1998) Chem Rev 98:1755–1785CrossRefGoogle Scholar
  78. 78.
    Chankvetadze B (2004) Chem Soc Rev 33:337–347CrossRefGoogle Scholar
  79. 79.
    Chankvetadze B, Fillet M, Burjanadze N, Bergenthal D, Bergander K, Luftmann H, Crommen J, Blaschke G (2000) Enantiomer 5:313–322Google Scholar
  80. 80.
    Servais AC, Rousseau A, Fillet M, Lomsadze K, Salgado A, Crommen J, Chankvetadze B (2010) J Sep Sci 33:1617–1624CrossRefGoogle Scholar
  81. 81.
    Chankvetadze B, Lomsadze K, Burjanadze N, Breitkrutz J, Pintore G, Chessa M, Bergander K, Blaschke G (2003) Electrophoresis 24:1083–1091CrossRefGoogle Scholar
  82. 82.
    Wei Y, Wang S, Chao J, Wang S, Cong C, Shuang S, Paau MC, Choi MMF (2011) J Phys Chem C 115:4033–4040CrossRefGoogle Scholar
  83. 83.
    Lomsadze K, Salgado A, Calvo E, Lopez JA, Chankvetadze B (2011) Electrophoresis 32:1156–1163CrossRefGoogle Scholar
  84. 84.
    Li W, Liu C, Tan G, Zhang X, Zhu Z, Chai Y (2012) Int J Mol Sci 13:710–725CrossRefGoogle Scholar
  85. 85.
    Vega ED, Lomsadze E, Chankvetadze L, Salgado A, Scriba GKE, Calvo E, López JA, Crego AL, Marina ML, Chankvetadze B (2011) Electrophoresis 32:2640–2647CrossRefGoogle Scholar
  86. 86.
    Lomsadze K, Vega ED, Salgado A, Crego AL, Scriba GKE, Marina ML, Chankvetadze B (2012) Electrophoresis (accepted)Google Scholar
  87. 87.
    Bednarek E, Wojciech B, Michalska K (2008) J Chromatogr A 1193:164–171CrossRefGoogle Scholar
  88. 88.
    Li W, Zhao L, Tan G, Sheng C, Zhang X, Zhu Z, Zhang G, Chai Y (2011) Chromatographia 73:1009–1014CrossRefGoogle Scholar
  89. 89.
    Li W, Tan G, Zhao L, Chen X, Zhang X, Zhu Z, Chai Y (2012) Anal Chim Acta 718:138–147CrossRefGoogle Scholar
  90. 90.
    Shi JH, Hu Y, Ding ZJ (2011) Comp Theor Chem 973:62–68CrossRefGoogle Scholar
  91. 91.
    Waibel B, Schreiber J, Meier C, Hammitzsch M, Baumann K, Scriba GKE, Holzgrabe U (2007) Eur J Org Chem 2921–2930Google Scholar
  92. 92.
    Bikádi Z, Fodor G, Hazai I, Hári P, Szemán J, Szente L, Fülöp F, Péter A, Hazai E (2010) Chromatographia 71:S21–S28CrossRefGoogle Scholar
  93. 93.
    Zhou ZM, Li X, Chen XP, Fang M, Dong X (2010) Talanta 82:775–784CrossRefGoogle Scholar
  94. 94.
    Li X, Zhou ZM, Xu D, Zhang J (2011) Talanta 84:1080–1092CrossRefGoogle Scholar
  95. 95.
    Shi JH, Ding ZJ, Hu Y (2011) Chromatographia 74:319–325CrossRefGoogle Scholar
  96. 96.
    Shi JH, Ding ZJ, Hu Y (2012) J Mol Model 18:803–813CrossRefGoogle Scholar
  97. 97.
    Issaraseriruk N, Shitangkoon A, Aree T (2010) J Mol Graph Mod 28:506–512CrossRefGoogle Scholar
  98. 98.
    Kawamura M, Uchiyama K, Kuramoto T, Tamura Y, Mizutani K (1989) Carbohydr Res 192:83–90CrossRefGoogle Scholar
  99. 99.
    Kawamura M, Uchiyama K (1994) Carbohydr Res 260:297–304CrossRefGoogle Scholar
  100. 100.
    Sun P, Wang C, Breitbach ZS, Zhang Y, Armstrong DW (2009) Anal Chem 81:10215–10226CrossRefGoogle Scholar
  101. 101.
    Jiang C, Tong M, Breitbach ZS, Armstrong DW (2009) Electrophoresis 30:1–14CrossRefGoogle Scholar
  102. 102.
    Sawada M, Tanaka T, Takai Y, Hanafusa T, Taniguchi T, Kawamura M, Uchiyama T (1991) Carbohydr Res 217:7–17CrossRefGoogle Scholar
  103. 103.
    Immel S, Schmitt GE, Lichtenthaler FW (1998) Carbohydr Res 217:7–17Google Scholar
  104. 104.
    Sun P, Armstrong DW (2010) J Chromatogr A 1217:4904–4918CrossRefGoogle Scholar
  105. 105.
    Kalíková K, Janečková L, Armstrong DW, Tesařová E (2911) J Chromatogr A 1218:1393–1398Google Scholar
  106. 106.
    Janečková L, Kalíková K, Vozka J, Armstrong DW, Bosárová Z, Tesařová E (2911) J Sep Sci 34:2639–2644Google Scholar
  107. 107.
    Zhang A, Armstrong DW (2011) Analyst 136:2931–2940CrossRefGoogle Scholar
  108. 108.
    Armstrong DW, Tang Y, Chen S, Zhou Y, Bagwill C, Chen JR (1994) Anal Chem 66:1473–1484CrossRefGoogle Scholar
  109. 109.
    Ilisz I, Berkecz R, Peter A (2006) J Sep Sci 29:1305–1321CrossRefGoogle Scholar
  110. 110.
    Ilisz I, Berkecz R, Peter A (2009) J Chromatogr A 1216:1845–1860CrossRefGoogle Scholar
  111. 111.
    Desiderio C, Fanali S (1998) J Chromatogr A 807:37–56CrossRefGoogle Scholar
  112. 112.
    Prokhorova A, Shapovalova EN, Shpigun OA (2010) J Pharm Biomed Anal 53:1170–1179Google Scholar
  113. 113.
    Berthod A (2009) Chirality 21:167–175CrossRefGoogle Scholar
  114. 114.
    Schäfer M, Schneider TR, Sheldrick GM (1996) Structure 4:1509–1515CrossRefGoogle Scholar
  115. 115.
    Loll PJ, Derhovanessian A, Shapovalov MV, Kaplan J, Yang L, Axelsen PH (2009) J Mol Biol 385:200–211CrossRefGoogle Scholar
  116. 116.
    Loll PJ, Kaplan J, Selinsky BS, Axelsen PH (1999) J Med Chem 42:4714–4719CrossRefGoogle Scholar
  117. 117.
    Lehmann C, Bunkoczi G, Vertesy L, Sheldrick GM (2002) J Mol Biol 318:723–732CrossRefGoogle Scholar
  118. 118.
    Bauvais C, Barbault F, Zhu Y, Petitjean M, Fan BT (2006) SAR QSAR Env Res 17:253–264CrossRefGoogle Scholar
  119. 119.
    Welch CJ (1994) J Chromatogr A 666:3–26CrossRefGoogle Scholar
  120. 120.
    Koscho ME, Spence PL, Pirkle WH (2005) Tetrahedron Asymmetry 16:3147–3153CrossRefGoogle Scholar
  121. 121.
    Del Rio A, Hayes JM, Stein M, Piras P, Roussel C (2004) Chirality 16:S1–S11CrossRefGoogle Scholar
  122. 122.
    Zhao CF, Cann NM (2008) Anal Chem 80:2426–2438CrossRefGoogle Scholar
  123. 123.
    Lämmerhofer M, Lindner W (1996) J Chromatogr A 741:33–48CrossRefGoogle Scholar
  124. 124.
    Mandl A, Nicoletti L, Lämmerhofer M, Lindner W (1999) J Chromatogr A 858:1–11CrossRefGoogle Scholar
  125. 125.
    Hoffmann CV, Lämmerhofer M, Lindner W (2007) J Chromatogr A 1161:242–251CrossRefGoogle Scholar
  126. 126.
    Hoffmann CV, Pell R, Lämmerhofer M, Lindner W (2008) Anal Chem 80:8780–8789CrossRefGoogle Scholar
  127. 127.
    Hoffmann CV, Reischl R, Maier NM, Lämmerhofer M, Lindner W (2009) J Chromatogr A 1216:1147–1156CrossRefGoogle Scholar
  128. 128.
    Lämmerhofer M, Lindner W (2008) In: Grushka E, Grushka N (eds) Advances in chromatography, vol 46. CRC Press, Boca Raton, pp 1–107Google Scholar
  129. 129.
    Czerwenka C, Lämmerhofer M, Maier NM, Rissanen K, Lindner W (2002) Anal Chem 74:5658–5666CrossRefGoogle Scholar
  130. 130.
    Maier NM, Schefzick S, Lombardo GM, Feliz M, Rissanen K, Lindner W, Lipkowitz KB (2002) J Am Chem Soc 124:8611–8629CrossRefGoogle Scholar
  131. 131.
    Hellriegel C, Skogsberg U, Albert K, Lämmerhofer M, Maier NM, Lindner W (2004) J Am Chem Soc 126:3809–3816CrossRefGoogle Scholar
  132. 132.
    Akasaka K, Gyimesi-Forras K, Lämmerhofer M, Fujita T, Watanabe M, Harada N, Lindner W (2005) Chirality 17:544–555CrossRefGoogle Scholar
  133. 133.
    Bicker W, Chiorescu I, Arion VB, Lämmerhofer M, Lindner W (2008) Tetrahedron Asymmetry 19:97–110CrossRefGoogle Scholar
  134. 134.
    Uccello-Barretta G, Balzano F, Salvadori P (2005) Chirality 17:S243–S248CrossRefGoogle Scholar
  135. 135.
    Maier NM, Nicoletti L, Lämmerhofer M, Lindner W (1999) Chirality 11:522–528CrossRefGoogle Scholar
  136. 136.
    Haginaka J (2000) J Chromatogr A 875:235–254CrossRefGoogle Scholar
  137. 137.
    Millot MC (2003) J Chromatogr B 797:131–159CrossRefGoogle Scholar
  138. 138.
    Haginaka J (2008) J Chromatogr B 875:12–19CrossRefGoogle Scholar
  139. 139.
    Guhman J, Zunszain PA, Petitpas I, Bhattacharya AA, Otagiri M, Curry S (2005) J Mol Biol 353:38–52CrossRefGoogle Scholar
  140. 140.
    Chuang VTG, Otagiri M (2006) Chirality 18:159–166CrossRefGoogle Scholar
  141. 141.
    Petitpas I, Bharracharya AA, Twine S, East M, Curry S (2001) J Biol Chem 276:22804–22809CrossRefGoogle Scholar
  142. 142.
    Stahlberg J, Henriksson H, Divne C, Isaksson R, Pettersson G, Johansson G, Jones TA (2001) J Mol Biol 305:79–93CrossRefGoogle Scholar
  143. 143.
    Pinkerton TC, Howe WJ, Ulrich EL, Comiskey JP, Haginaka J, Murashima T, Walkenhorst WF, Westler WW, Markley JL (1995) Anal Chem 67:2254–2367CrossRefGoogle Scholar
  144. 144.
    Matsunaga M, Haginaka J (2006) J Chromatogr A 1106:124–130CrossRefGoogle Scholar
  145. 145.
    Zsila F, Isao Y (2007) Biochim Biophys Acta 1770:797–809CrossRefGoogle Scholar
  146. 146.
    Lavecchia A, Cosconati W, Novellino E, Calleri E, Temporini C, Massolini G, Carbonara G, Fracchiolla G, Loiodice F (2007) J Mol Graphics Modell 25:773–783CrossRefGoogle Scholar
  147. 147.
    Massolini G, Temporini C, Calleri E (2008) J Chromatogr B 875:20–29CrossRefGoogle Scholar
  148. 148.
    Hu Z, Jiang J (2009) J Phys Chem B 113:15851–15857CrossRefGoogle Scholar
  149. 149.
    Ranieri DI, Hofstetter H, Hofstetter O (2009) J Sep Sci 32:1686–1695CrossRefGoogle Scholar
  150. 150.
    Haginaka J (2011) In: Grushka E (ed) Advances in chromatography, vol 49. CRC Press, Boca Raton, pp 37–69Google Scholar
  151. 151.
    Zheng Y, Wang X, Ji Y (2012) Talanta 91:7–17CrossRefGoogle Scholar
  152. 152.
    Blaschke G, Bröker W, Fränkel W (1986) Angew Chem Int Ed Engl 25:830–831CrossRefGoogle Scholar
  153. 153.
    Allenmark SG, Andersson S, Möller P, Sanchez D (1995) Chirality 7:248–256CrossRefGoogle Scholar
  154. 154.
    Zhong Q, Han X, He L, Beesley TE, Trahanovsky WS, Armstrong DW (2005) J Chromatogr A 1066:55–70CrossRefGoogle Scholar
  155. 155.
    Okamoto Y, Suzuki K, Ohta K, Hatada K, Yuki H (1979) J Am Chem Soc 101:4763–4765CrossRefGoogle Scholar
  156. 156.
    Miyabe T, Ida H, Ohnishi A, Yashima E (2012) Chem Sci 3:863–867CrossRefGoogle Scholar
  157. 157.
    Tamura K, Miyabe T, Ida H, Yashima E (2011) Polym Chem 2:91–98CrossRefGoogle Scholar
  158. 158.
    Gasparrini F, Misiti D, Rompietti R, Villani C (2005) J Chromatogr A 1064:25–38CrossRefGoogle Scholar
  159. 159.
    Sellergren B (2007) In: Subraimanian G (ed) Chiral separation techniques, 3rd edn. Wiley-VCH, Weinheim, pp 399–431Google Scholar
  160. 160.
    Turiel E, Martin-Esteban A (2004) Anal Bioanal Chem 378:1876–1886CrossRefGoogle Scholar
  161. 161.
    Dong H, Tong F, Li J, Wang Z, Wang Y, Shen X (2011) Adv Mat Res 150–151:150–159CrossRefGoogle Scholar
  162. 162.
    Luo Y, Liu L, Li L, Deng Q (2007) Chromatographia 65:675–679CrossRefGoogle Scholar
  163. 163.
    Katz A, Davis ME (1999) Macromolecules 32:4113–4121CrossRefGoogle Scholar
  164. 164.
    Jiang J, Song K, Chen Z, Zhou Q, Tang Y, Gu F, Zuo X, Xu Z (2011) J Chromatogr A 1218:3763–3770CrossRefGoogle Scholar
  165. 165.
    Piletsky SA, Karim K, Piletska EV, Day CJ, Freebairn KW, Legge C, Turner APF (2001) Analyst 126:1826–1830CrossRefGoogle Scholar
  166. 166.
    Zhou Q, He J, Tang Y, Xu X, Li H, Kang C, Jiang J (2012) J Chromatogr A 1238:60–67CrossRefGoogle Scholar
  167. 167.
    Rong F, Li P (2012) Adv Mat Res 391–392:111–115Google Scholar
  168. 168.
    Maier NM, Lindner W (2007) Anal Bioanal Chem 389:377–397CrossRefGoogle Scholar
  169. 169.
    Davankov VA, Rogozhin SV (1971) J Chromatogr 60:284–312CrossRefGoogle Scholar
  170. 170.
    Gassmann E, Kuo JE, Zare R (1985) Science 230:813–814CrossRefGoogle Scholar
  171. 171.
    Schmid MG, Gübitz G (2011) Anal Bioanal Chem 400:2305–2316CrossRefGoogle Scholar
  172. 172.
    Aizawa S, Yamamoto A, Kodama S (2006) Electrophoresis 27:880–886CrossRefGoogle Scholar
  173. 173.
    Davankov VA (2003) J Chromatogr A 1000:891–915CrossRefGoogle Scholar
  174. 174.
    Aizawa S, Kodama S (2012) Electrophoresis 33:523–527CrossRefGoogle Scholar
  175. 175.
    Mofaddel N, Adoubel AA, Morin CJ, Desbene PL, Dupas G (2010) J Mol Struct 975:220–226CrossRefGoogle Scholar
  176. 176.
    Chen Z, Uchiyama K, Hobo T (2000) Anal Sci 16:837–841CrossRefGoogle Scholar
  177. 177.
    Maccarrone G, Contino A, Cucinotta V (2012) Tends Anal Chem 32:133–153CrossRefGoogle Scholar
  178. 178.
    Shtyrlin VG, Zyavkina YI, Gilyazetdinov EM, Burkharov MS, Krutikov AA, Garipov RR, Mukhtarov AS, Zakharov AV (2012) Dalton Trans 41:1216–1228CrossRefGoogle Scholar
  179. 179.
    Cucinotta V, Giuffrida A, Maccarrone G, Messina M, Puglisi A, Rizzarelli E, Vecchio G (2005) Dalton Trans 2731–2736Google Scholar
  180. 180.
    Natalini B, Giacchè N, Sardella R, Ianni F, Macchiarulo A, Pellicciari R (2010) J Chrom A 1217:7523–7527CrossRefGoogle Scholar
  181. 181.
    Dimitrova P, Bart HJ (2011) Open Proc Chem J 4:1–7CrossRefGoogle Scholar
  182. 182.
    Gübitz G, Schmid MG (2007) In: Subraimanian G (ed) Chiral separation techniques, 3rd edn. Wiley-VCH, Weinheim, pp 155–179Google Scholar
  183. 183.
    Kartsova LA, Alekseeva AV (2011) J Anal Chem 66:563–571CrossRefGoogle Scholar
  184. 184.
    Bang E, Jung JW, Lee W, Lee DW, Lee W (2001) J Chem Soc Perkin Trans 2:1685–1692Google Scholar
  185. 185.
    Lee W, Bang E, Baek CS, Lee W (2004) Magn Res Chem 42:389–395CrossRefGoogle Scholar
  186. 186.
    Nagata H, Nishi H, Kamagauchi M, Ishida T (2004) Org Biomol Chem 2:3470–3475CrossRefGoogle Scholar
  187. 187.
    Nagata H, Nishi H, Kamagauchi M, Ishida T (2008) Chirality 20:820–827CrossRefGoogle Scholar
  188. 188.
    Nagata H, Machida Y, Nishi H, Kamigauchi M, Minoura K, Ishida T (2009) Bull Chem Soc Jpn 82:219–229CrossRefGoogle Scholar
  189. 189.
    Nagata H, Nishi H, Kamigauchi M, Ishida T (2006) Chem Pharm Bull 54:452–557CrossRefGoogle Scholar
  190. 190.
    Gerbaux P, De Winter J, Cornil D, Ravicini K, Pesesse G, Cornil J, Flammang R (2008) Chem Eur J 14:11039–11049CrossRefGoogle Scholar
  191. 191.
    Hyun MH (2006) J Sep Sci 29:750–761CrossRefGoogle Scholar
  192. 192.
    Cho HJ, Hyun MH (2007) J Liq Chromatogr Rel Technol 30:853–875CrossRefGoogle Scholar
  193. 193.
    Cho SH, Choi HJ, Hyun MH (2009) J Chromatogr A 1216:7446–7449CrossRefGoogle Scholar
  194. 194.
    Cho SH, Choi HJ, Lee A, Jin JS, Jeong ED, Hyun MH (2009) Bull Korr Chem Soc 30:1903–1905CrossRefGoogle Scholar
  195. 195.
    Kuhn R (1999) Electrophoresis 20:2605–2613CrossRefGoogle Scholar
  196. 196.
    Elbashir AA, Aboul-Enein HY (2010) Curr Pharm Anal 6:101–113CrossRefGoogle Scholar
  197. 197.
    Li SY, Xu YW, Liu YW, Su CY (2011) Int J Mol Sci 12:429–455CrossRefGoogle Scholar
  198. 198.
    Sirit A, Yilmaz M (2009) Turk J Chem 33:159–200Google Scholar
  199. 199.
    Pfeiffer J, Schurig V (1999) J Chromatogr A 840:145–150CrossRefGoogle Scholar
  200. 200.
    Healy LO, McEnery MM, McCarthy DG, Harris SJ, Glennon JD (1996) Anal Lett 31:1543–1551CrossRefGoogle Scholar
  201. 201.
    Sokoliess T, Opolka A, Meynes U, Roth U, Jira T (2002) Pharmazie 57:589–590Google Scholar
  202. 202.
    Krawinkler KH, Maier NM, Sajovic E, Lindner W (2004) J Chromatogr A 1053:119–131Google Scholar
  203. 203.
    Thamarai Chelvi SK, Yong EL, Gong Y (2008) J Chromatogr A 1203:54–58CrossRefGoogle Scholar
  204. 204.
    Pena MS, Zhang Y, Warner IM (1997) Anal Chem 69:3239–3242CrossRefGoogle Scholar
  205. 205.
    Grady T, Joyce T, Smyth MR, Diamond D, Harris SJ (1998) Anal Commun 35:123–125CrossRefGoogle Scholar
  206. 206.
    Meyer R, Jira T (2007) Curr Anal Chem 3:161–170CrossRefGoogle Scholar
  207. 207.
    Ellington AD, Szostak JW (1990) Nature 346:818–822CrossRefGoogle Scholar
  208. 208.
    Ellington AD, Szostak JW (1992) Nature 355:850–852CrossRefGoogle Scholar
  209. 209.
    Geiger A, Burgstaller P, von der Eltz H, Roeder A, Famulok M (1996) Nucl Acid Res 24:1029–1036CrossRefGoogle Scholar
  210. 210.
    Shoji A, Kuwahara M, Ozaki H, Sawai H (2007) J Am Chem Soc 129:1456–1464CrossRefGoogle Scholar
  211. 211.
    Patel DJ, Suri AK, Jiang F, Jiang L, Fan P, Kumar RA, Nonin S (1997) J Mol Biol 272:645–664CrossRefGoogle Scholar
  212. 212.
    Robertson SA, Harada K, Frankel AD, Wemmer DE (2000) Biochemistry 39:946–954CrossRefGoogle Scholar
  213. 213.
    Lin CH, Patel DJ (1996) Nat Struct Biol 3:1046–1050CrossRefGoogle Scholar
  214. 214.
    Hermann T, Patel DJ (2000) Science 287:820–825CrossRefGoogle Scholar
  215. 215.
    Yang X, Bing T, Mei H, Fang C, Cao Z, Shangguan D (2011) Analyst 36:577–585CrossRefGoogle Scholar
  216. 216.
    Bishop GR, Ren J, Polander BC, Jeanfreau BD, Trent JO, Chaires JB (2007) Biophys Chem 126:165–175CrossRefGoogle Scholar
  217. 217.
    Jucker FM, Phillips RM, McCallum SA, Pardi A (2003) Biochemistry 42:2560–2567CrossRefGoogle Scholar
  218. 218.
    Michaud M, Jourdan E, Ravelet C, Villet A, Ravel A, Grosset C, Peyrin E (2004) Anal Chem 76:1015–1020CrossRefGoogle Scholar
  219. 219.
    Michaud M, Jourdan E, Villet A, Ravel A, Grosset C, Pyerin E (2003) J Am Chem Soc 125:8672–8679CrossRefGoogle Scholar
  220. 220.
    Ravelet C, Boulkedid R, Ravel A, Grosset C, Villet A, Fize J, Peyrin E (2005) J Chromatogr A 1076:62–70CrossRefGoogle Scholar
  221. 221.
    Ruta J, Grosset C, Ravelet C, Fize J, Villet A, Peyrin E (2007) J Chromatogr B 845:186–190CrossRefGoogle Scholar
  222. 222.
    Ruta J, Ravelet C, Grosset C, Fize J, Ravel A, Villet A, Peyrin E (2006) Anal Chem 78:3032–3029Google Scholar
  223. 223.
    Ruta J, Ravelet C, Baussanne I, Decout JL, Peyrin E (2007) Anal Chem 97:4716–4719CrossRefGoogle Scholar
  224. 224.
    Ruta J, Perrier S, Ravelet C, Roy B, Perigaud C, Peyrin E (2009) Anal Chem 81:1169–1176CrossRefGoogle Scholar
  225. 225.
    Andre C, Berthelot A, Thomassin M, Guillaume YC (2006) Electrophoresis 27:3254–3262CrossRefGoogle Scholar
  226. 226.
    Ravelet C, Peyrin E (2006) J Sep Sci 2:1322–1331CrossRefGoogle Scholar
  227. 227.
    Peyrin E (2009) J Sep Sci 32:1531–1536CrossRefGoogle Scholar
  228. 228.
    Wang J, Warner IM (1994) Anal Chem 66:3773–3776CrossRefGoogle Scholar
  229. 229.
    Dobashi A, Hamada M, Dobashi Y, Yamaguchi J (1995) Anal Chem 67:3011–3017CrossRefGoogle Scholar
  230. 230.
    Dey J, Ghosh A (2010) In: Van Eeckhaut A, Michotte Y (eds) Chiral separations by capillary electrophoresis. CRC Press, Boca Raton, pp 195–234Google Scholar
  231. 231.
    Otsuka K, Terabe S (2000) J Chromatogr A 875:163–178CrossRefGoogle Scholar
  232. 232.
    El Rassi Z (2000) J Chromatogr A 875:207–233CrossRefGoogle Scholar
  233. 233.
    Shamsi SA, Palmer CP, Warner IM (2001) Anal Chem 73:140A–149AGoogle Scholar
  234. 234.
    Yarabe HH, Billot E, Warner IM (2000) J Chromatogr A 875:179–206CrossRefGoogle Scholar
  235. 235.
    Hebling CM, Thompson LE, Eckenroad KW, Manley GA, Fry RA, Mueller KT, Strein TG, Rovnyak D (2008) Langmuir 24:13866–13874CrossRefGoogle Scholar
  236. 236.
    Rugutt JK, Billot E, Warner IM (2000) Langmuir 16:3022–3029CrossRefGoogle Scholar
  237. 237.
    Kingsbury SA, Ducommun CJ, Zahakaylo BM, Dickinson EH, Morris KF (2010) Magn Reson Chem 48:184–191Google Scholar
  238. 238.
    Valle BC, Morris KF, Fletcher KA, Fernand V, Sword DM, Eldridge S, Larive CK, Warner IM (2007) Langmuir 23:425–435CrossRefGoogle Scholar
  239. 239.
    Morris KF, Becker BA, Valle BC, Warner IM, Larive CK (2006) J Phys Chem B 110:17359–17369CrossRefGoogle Scholar
  240. 240.
    Yarabe HH, Rugutt JK, McCarroll ME, Warner IM (2000) Electrophoresis 21:2025–2032CrossRefGoogle Scholar
  241. 241.
    Bica K, Gaertner P (2008) Eur J Org Chem 19:3235–3250CrossRefGoogle Scholar
  242. 242.
    Ding J, Welton T, Armstrong DW (2004) Anal Chem 76:6819–6822CrossRefGoogle Scholar
  243. 243.
    Zhao L, Ali P, Duan AH, Yuan LM (2011) Anal Bioanal Chem 399:143–147CrossRefGoogle Scholar
  244. 244.
    Zhou Z, Li X, Chen X, Hao X (2010) Anal Chim Acta 678:208–214CrossRefGoogle Scholar
  245. 245.
    Liu Q, Wu K, Tang F, Yao L, Yang F, Nie Z, Yao S (2009) Chem Eur J 15:9889–9896CrossRefGoogle Scholar
  246. 246.
    Francois Y, Varenne A, Juillerat E, Villemin D, Gareil P (2007) J Chromatogr A 1155:134–141CrossRefGoogle Scholar
  247. 247.
    Tran CD, Mejac I (2008) J Chromatogr A 1204:204–209CrossRefGoogle Scholar
  248. 248.
    Ma Z, Zhang L, Lin L, Ji P, Guo X (2010) Biomed Chromatogr 24:1332–1337CrossRefGoogle Scholar
  249. 249.
    Rizvi SAA, Shamsi SA (2006) Anal Chem 78:7061–7069CrossRefGoogle Scholar
  250. 250.
    Bi W, Tian M, Row KH (2011) Analyst 136:379–387CrossRefGoogle Scholar
  251. 251.
    Shamsi SA, Danielson ND (2007) J Sep Sci 30:1729–1750CrossRefGoogle Scholar
  252. 252.
    Pino V, German-Hernandez M, Martin-Perez A, Anderson JL (2012) Sep Sci Technol 47:264–276CrossRefGoogle Scholar
  253. 253.
    Bwambok DK, Marwani HM, Fernand VE, Eakayode SO, Lowry M, Negulescu I, Strongin RM, Warner IM (2008) Chirality 20:151–158CrossRefGoogle Scholar
  254. 254.
    De Rooy A, Li M, Bwambok DK, El-Zahab B, Challa S, Warner IM (2011) Chirality 23:54–62CrossRefGoogle Scholar
  255. 255.
    Kroupa DM, Brown CJ, Heckman LM Hopkins TA (2012) J Phys Chem B. doi:  10.1021/jp300357z
  256. 256.
    Gasparrini F, Misiti D, Pierini M, Villani C (2002) Org Lett 4:3993–3996CrossRefGoogle Scholar
  257. 257.
    Uccello-Barretta G, Balzano F, Martinelli J, Gasparrini F, Pierini M, Villani C (2011) Eur J Org Chem 3738–3747Google Scholar
  258. 258.
    Dong Y, McGown LB (2011) Electrophoresis 32:1735–1741CrossRefGoogle Scholar
  259. 259.
    Davis JT (2004) Angew Chem Int Ed 43:668–698CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  1. 1.Department of Pharmaceutical/Medicinal ChemistryFriedrich Schiller University JenaJenaGermany

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