Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry

Journal of Chromatography A

Volumn 1337, Issue , 2014, Pages 85-94

  Hettegger, Hubert ^a   Kohout, Michal ^b   Mimini, Vebi ^a   Lindner, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Chiral anion exchange chromatography; Cinchona alkaloids; Click chemistry; Copper catalysis; Enantiomer separation; Liquid chromatography

Indexed keywords

CHIRAL ANIONS; CINCHONA ALKALOID; CLICK CHEMISTRY; COPPER-CATALYSIS; ENANTIOMER SEPARATION;

HYDROCARBONS; ION EXCHANGE RESINS; LIQUID CHROMATOGRAPHY; NITROGEN COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

LOADING;

1,2,3 TRIAZOLE DERIVATIVE; ALKYNE; AZIDE; CARBOXYLIC ACID DERIVATIVE; COPPER; QUINIDINE; QUININE; SCAVENGER; SILICON DIOXIDE; THIOL;

ANION EXCHANGE CHROMATOGRAPHY; ARTICLE; CARBAMOYLATION; CHEMICAL BINDING; CHEMICAL COMPOSITION; CHIRAL CHROMATOGRAPHY; CINCHONA; CLICK CHEMISTRY; CYCLOADDITION; DENSITY; ENANTIOSELECTIVITY; IMMOBILIZATION; NONHUMAN; PHASE SEPARATION; PRIORITY JOURNAL; STEREOSPECIFICITY; SYNTHESIS;

CINCHONA;

CHIRAL ANION EXCHANGE CHROMATOGRAPHY; CINCHONA ALKALOIDS; CLICK CHEMISTRY; COPPER-CATALYSIS; ENANTIOMER SEPARATION; LIQUID CHROMATOGRAPHY;

ALKYNES; AMINO ACIDS; AZIDES; CARBAMATES; CHROMATOGRAPHY; CLICK CHEMISTRY; CYCLOADDITION REACTION; ION EXCHANGE; QUINIDINE; QUININE; SILICON DIOXIDE; STEREOISOMERISM;

EID: 84900627864     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2014.02.026     Document Type: Article

References (56)

1. Francotte E.R. J. Chromatogr. A 1994, 666:565.
2. Francotte E.R., Junker-Buchheit A. J. Chromatogr. Biomed. Appl. 1992, 576:1.
3. Francotte E.R. J. Chromatogr. A 2001, 906:379.
4. Bicchi C., D'Amato A., Rubiolo P. J. Chromatogr. A 1999, 843:99.
5. Betts T.J. J. Chromatogr. A 2001, 936:33.
6. Vetter W., Schurig V. J. Chromatogr. A 1997, 774:143.
7. Cochran J.W., Frame G.M. J. Chromatogr. A 1999, 843:323.
8. Bester K. Anal. Bioanal. Chem. 2003, 376:302.
9. Ahmed F.E. TrAC Trends Anal. Chem. 2003, 22:170.
10. Smith N.W., Evans M.B. Chromatographia 1994, 38:649.
11. Euerby M.R., Johnson C.M., Bartle K.D., Myers P., Roulin S.C.P. Anal. Commun. 1996, 33:403.
12. Maier N.M., Franco P., Lindner W. J. Chromatogr. A 2001, 906:3.
13. Han S., Row K. Chin. J. Chem. Eng. 2005, 13:741.
14. Laemmerhofer M., Lindner W. J. Chromatogr. A 1998, 829:115.
15. He L., Beesley T.E. J. Liq. Chromatogr. Relat. Technol. 2005, 28:1075.
16. Ribeiro A.E., Gomes P.S., Pais L.S., Rodrigues A.E. Sep. Sci. Technol. 2011, 46:1726.
17. Ribeiro S.S., Raminelli C., Porto A.L.M. J. Fluorine Chem. 2013, 154:53.
18. Lorenz H., Perlberg A., Sapoundjiev D., Elsner M.P., Seidel-Morgenstern A. Chem. Eng. Process. 2006, 45:863.
19. Hellinger R., Horak J., Lindner W. Anal. Bioanal. Chem. 2013, 405:8105.
20. Miyabe T., Iida H., Ohnishi A., Yashima E. Chem. Sci. 2012, 3:863.
21. Xue-Feng X.U., Zhi-Mou G.U.O., LIANG Xin-Miao. Separation of benzoxazine enantiomers on β-cyclodextrin bonded chiral stationary phases[J]. Chinese Journal of Chromatography 2012, 30(11):1188-1193. 10.3724/SP.J.1123.2012.02011.
22. Gondova T.A., Petrovaj J., Sucha M., Armstrong D.W. J. Liq. Chromatogr. Relat. Technol. 2011, 34:2304.
23. Park S., Kim S.J., Hyun M.H. Bull. Korean Chem. Soc. 2012, 33:3497.
24. Laemmerhofer M. J. Chromatogr. A. 2010, 1217:814.
25. Pirkle W.H., Pochapsky T.C. Chem. Rev. 1989, 89:347.
26. Hoffmann C.V., Laemmerhofer M., Lindner W. J. Chromatogr. A. 2007, 1161:242.
27. Gargano A.F.G., Kohout M., Macikova P., Laemmerhofer M., Lindner W. Anal. Bioanal. Chem. 2013, 405:8027.
28. Hoffmann C.V., Pell R., Lammerhofer M., Lindner W. Anal. Chem. 2008, 80:8780.
29. Hoffmann C.V., Reischl R., Maier N.M., Laemmerhofer M., Lindner W. J. Chromatogr. A. 2009, 1216:1147.
30. Hoffmann C.V., Pell R., Laemmerhofer M., Lindner W. Anal. Chem. (Washington, DC, U.S.) 2008, 80:8780.
31. Kacprzak K.M., Lindner W. J. Sep. Sci. 2011, 34:2391.
32. Mandl A., Nicoletti L., Lammerhofer M., Lindner W. J. Chromatogr. A 1999, 858:1.
33. Oberleitner W.R., Maier N.M., Lindner W. J. Chromatogr. A 2002, 960:97.
34. Rostovtsev V.V., Green L.G., Fokin V.V., Sharpless K.B. Angew. Chem. Int. Ed. 2002, 41:2596.
35. Kacprzak K.M., Maier N.M., Lindner W. J. Chromatogr. A. 2011, 1218:1452.
36. Tornoe C.W., Christensen C., Meldal M. J. Org. Chem. 2002, 67:3057.
37. Boren B.C., Narayan S., Rasmussen L.K., Zhang L., Zhao H., Lin Z., Jia G., Fokin V.V. J. Am. Chem. Soc. 2008, 130:8923.
38. Barra M., Roy O., Traikia M., Taillefumier C. Org. Biomol. Chem. 2010, 8:2941.
39. Wernisch S., Pell R., Lindner W. J. Sep. Sci. 2012, 35:1560.
40. Laemmerhofer M., Lindner W. J. Chromatogr. A 1996, 741:33.
41. Maier N.M., Nicoletti L., Lammerhofer M., Lindner W. Chirality 1999, 11:522.
42. Laemmerhofer M., Di Eugenio P., Molnar I., Lindner W. J. Chromatogr. B Biomed. Appl. 1997, 689:123.
43. Piette V., Lammerhofer M., Bischoff K., Lindner W. Chirality 1997, 9:157.
44. Picha J., Budesinsky M., Hanclova I., Sanda M., Fiedler P., Vanek V., Jiracek J. Tetrahedron 2009, 65:6090.
45. Gavioli E., Maier N.M., Haupt K., Mosbach K., Lindner W. Anal. Chem. 2005, 77:5009.
46. Wolrab D., Fruehauf P., Kohout M., Lindner W. J. Sep. Sci. 2013, 36:2826.
47. Ichikawa M., Ohtsuka M., Ohki H., Haginoya N., Itoh M., Sugita K., Usui H., Suzuki M., Terayama K., Kanda A. Bioorg. Med. Chem. 2012, 20:3072.
48. Kacprzak K.M., Maier N.M., Lindner W. Tetrahedron Lett. 2006, 47:8721.
49. Maier N.M. Chromatogr. Today 2009, 2009:3.
50. Li G.-X., Liu Z.-Q., Luo X.-Y. Eur. J. Med. Chem. 2010, 45:1821.
51. Dijkstra G.D.H., Kellogg R.M., Wynberg H., Svendsen J.S., Marko I., Sharpless K.B. J. Am. Chem. Soc. 1989, 111:8069.
52. Czerwenka C., Laemmerhofer M., Maier N.M., Rissanen K., Lindner W. Anal. Chem. 2002, 74:5658.
53. Marshall M.A., Mottola H.A. Anal. Chem. 1985, 57:375.
54. Levkin P., Maier N.M., Lindner W., Schurig V. J. Chromatogr. A. 2012, 1269:270.
55. Krawinkler K.H., Gavioli E., Maier N.M., Lindner W. Chromatographia 2003, 58:555.
56. Laemmerhofer M., Lindner W. Advances in Chromatography 2008, 1. CRC Press, Boca Raton, FL. E. Grushka, N. Grinberg (Eds.).