Triazolo-linked cinchona alkaloid carbamate anion exchange-type chiral stationary phases: Synthesis by click chemistry and evaluation

Journal of Chromatography A

Volumn 1218, Issue 11, 2011, Pages 1452-1460

  Kacprzak, Karol M ^a   Maier, Norbert M ^b   Lindner, Wolfgang ^b  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

Chiral stationary phases; Chromatography; Cinchona alkaloids; Click chemistry; Enantiomer separation; Immobilization

Indexed keywords

CHIRAL STATIONARY PHASIS; CINCHONA ALKALOIDS; CLICK CHEMISTRY; ENANTIOMER SEPARATION; IMMOBILIZATION;

CHIRALITY; CYCLOADDITION; ENANTIOMERS; ENANTIOSELECTIVITY; METABOLITES; NITROGEN COMPOUNDS; SILICA; SILICA GEL;

CHROMATOGRAPHY;

1,2,3 TRIAZOLE DERIVATIVE; 10,11 DIDEHYDROCINCHONA TERT BUTYLCARBAMATE DERIVATIVE; AMINO ACID DERIVATIVE; AROMATIC CARBOXYLIC ACID; ARYLOXYCARBOXYLIC ACID; BINAPHTHOL PHOSPHATE; CARBAMIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PHOSPHATE; SILICON DIOXIDE; SULFIDE; UNCLASSIFIED DRUG;

ANION EXCHANGE CHROMATOGRAPHY; ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRAL STATIONARY PHASE; CHIRALITY; CLICK CHEMISTRY; CONTINUOUS PROCESS; CONTROLLED STUDY; CYCLOADDITION; ENANTIOSELECTIVITY; EVALUATION RESEARCH; MOLECULAR RECOGNITION; MOLECULAR STABILITY; PHASE SEPARATION; PHYSICAL PHASE; PRIORITY JOURNAL; PROCESS CONTROL; RACEMIC MIXTURE; REVERSED PHASE LIQUID CHROMATOGRAPHY; SYNTHESIS;

CARBAMATES; CHROMATOGRAPHY; CINCHONA ALKALOIDS; CLICK CHEMISTRY; STEREOISOMERISM;

CINCHONA;

EID: 79951720434     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chroma.2011.01.031     Document Type: Article

References (50)

1. Okamoto Y., Ikai T. Chem. Soc. Rev. 2008, 37:2593.
2. Francotte E.R. J. Chromatogr. A 2001, 906:379.
3. Buchmeiser M.R. J. Chromatogr. A 2001, 918:233.
4. Krawinkler K.H., Gavioli E., Maier N.M., Lindner W. Chromatographia 2003, 58:555.
5. Götmar G., Fornstedt T., Guiochon G. Chirality 2000, 12:558.
6. Fornstedt T., Sajonz P., Guiochon G. Chirality 1998, 10:375.
7. Haginaka J., Okazaki Y., Matsunaga H. J. Chromatogr. A 1999, 840:171.
8. Hahn R., Amatschek K., Schallaun E., Necina R., Josic D., Jungbauer A. Int. J. Biochromatogr. 2000, 5:175.
9. Brogan K.L., Schoenfisch M.H. Langmuir 2005, 21:3054.
10. Tornoe C.W., Christensen C., Meldal M. J. Org. Chem. 2002, 67:3057.
11. Rostovtsev V.V., Green L.G., Fokin V.V., Sharpless K.B. Angew. Chem. Int. Ed. 2002, 41:2596.
12. Punna S., Kaltgrad E., Finn M.G. Bioconjugate Chem. 2005, 16:1536.
13. Slater M., Snauko M., Svec F., Frechet J.M.J. Anal. Chem. 2006, 78:4969.
14. Guo Z., Lei A., Liang X., Xu Q. Chem. Commun. 2006, 4512.
15. Guo Z., Lei A., Zhang Y., Xu Q., Xue X., Zhang F., Liang X. Chem. Commun. 2007, 2491.
16. Fu Q., Guo Z., Liang T., Zhang X., Xu Q., Liang X. Anal. Methods 2010, 3:217.
17. Huang H., Jin Y., Xue M., Yu L., Fu Q., Ke Y., Chu C., Liang X. Chem. Commun. 2009, 6973.
18. Xue M., Huang H., Ke Y., Chu C., Jin Y., Liang X. J. Chromatogr. A 2009, 1216:8623.
19. Guo Z., Liu Y., Xu J., Xu Q., Xue X., Zhang F., Ke Y., Liang X., Lei A. J. Chromatogr. A 2008, 1191:78.
20. Ortega-Muñoz M., Lopez-Jaramillo J., Hernandez-Mateo F., Santoyo-Gonzalez F. Adv. Synth. Catal. 2006, 348:2410.
21. Santoyo-Gonzalez F., Hernandez-Mateo F. Chem. Soc. Rev. 2009, 38:3449.
22. Moni L., Ciogli A., D'Acquarica I., Dondoni A., Gasparrini F., Marra A. Chem. Eur. J. 2010, 16:5712.
23. Suksrichavalit T., Yoshimatsu K., Prachayasittikul V., Bülow L., Ye L. J. Chromatogr. A 2010, 1217:3635.
24. Kacprzak K., Maier N., Lindner W. Tetrahedron Lett. 2006, 47:8721.
25. Kacprzak K., Maier N., Lindner W. J. Sep. Sci. 2010, 33:2590.
26. Zhang Y., Guo Z., Ye J., Xu Q., Liang X., Lei A. J. Chromatogr. A 2008, 1191:188.
27. Wang Y., Xiao Y., Tan T.T.Y., Ng S.-Ch. Tetrahedron Lett. 2008, 49:5190.
28. Guo Z., Jin Y., Liang T., Liu Y., Xu Q., Liang X., Lei A. J. Chromatogr. A 2009, 1216:257.
29. Wang Y., Ong T.-T., Li L.-S., Tan T.T.Y., Ng S.-C. J. Chromatogr. A 2009, 1216:2388.
30. Feng J.-T., Guo Z., Shi H., Gu J., Jin Y., Liang X. Talanta 2010, 81:1870.
31. Wang Y., Xiao Y., Tan T.T.Y., Ng S.-C. Electrophoresis 2009, 30:705.
32. Slater M.D., Fréchet J.M.J., Svec F. J. Sep. Sci. 2009, 32:21.
33. Sun X., Lin D., He X., Chen L., Zhang Y. Talanta 2010, 82:404.
34. Kacprzak K., Lindner W., Maier N. Chirality 2007, 20:441.
35. Mandl A., Nicoletti L., Lämmerhofer M., Lindner W. J. Chromatogr. A 1999, 858:1.
36. Binder W.H., Kluger Ch. Curr. Org. Chem. 1791, 10(2006).
37. Wu P., Fokin V.V. Aldrichim. Acta 2007, 40:7.
38. Zamolo L., Salvalaglio M., Cavallotti C., Galarza B., Sadler C., Williams S., Hofer S., Horak J., Lindner W. J. Phys. Chem. B 2010, 114:9367.
39. Lämmerhofer M., Lindner W. Chromatogr. Adv. 2008, 46:1.
40. Kacprzak K., Gawroński J. Cinchona Alkaloids in Synthesis & Catalysis 2009, Wiley-VCH, Weinheim. C. Song (Ed.).
41. Hellriegel C., Skogsberg U., Albert K., Lammerhofer M., Maier N.M., Lindner W. J. Am. Chem. Soc. 2004, 126:3809.
42. Maier N.M., Schefzick S., Lombardo G.M., Feliz M., Rissanen K., Lindner W., Lipkowitz K.B. J. Am. Chem. Soc. 2002, 124:8611.
43. Krawinkler K.H., Maier N.M., Sajovic E., Lindner W. J. Chromatogr. A 2004, 1053:119.
44. Franco P., Lämmerhofer M., Klaus P.M., Lindner W. J. Chromatogr. A 2000, 869:111.
45. Lämmerhofer M., Lindner W. J. Chromatogr. A 1996, 741:33.
46. Pirkle W.H., Welch C.J. J. Liquid Chromatogr. 1992, 15:1947.
47. Uray G., Maier N.M. Enantiomer 1996, 1:211.
48. Brüggemann J., Bitter S., Müller S., Müller W.M., Müller U., Maier N.M., Lindner W., Vögtle F. Angew. Chem. Int. Ed. 2007, 46:254.
49. Kolb H.C., Sharpless K.B. Drug Discov. Today 2003, 8:1128.
50. Bourne Y., Radić Z., Kolb H.C., Sharpless K.B., Taylor P., Marchot P. Chem. Biol. Interact. 2005, 157-158:159.