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http://dx.doi.org/10.5012/bkcs.2006.27.11.1775

Resolution of β-Amino Acids on a Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxilic Acid without Extra Free Aminopropyl Groups on Silica Surface  

Hyun, Myung- Ho (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National UniversityDepartment of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
Choi, Hee-Jung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
Kang, Bu-Sung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
Tan, Guang-Hui (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
Cho, Yoon-Jae (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
Publication Information
Abstract
A liquid chromatographic chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxilic acid without extra free aminopropyl groups on silica surface has been demonstrated to be quite effective for the resolution of various $\beta$-amino acids. The retention factors ($k_1$) for the resolution of $\beta$-amino acids on the CSP were quite large and the large retention factors might be quite attractive along with the reasonable separation factors ($\alpha$) for preparative scale enantioselective chromatography. The large retention factors on the CSP were found to be reduced effectively by adding ammonium ion to mobile phase without sacrificing the chiral recognition efficiency of the CSP. Consequently, the CSP is also quite applicable for use in analytical enantioselective chromatography.
Keywords
beta-Amino acids; Chiral stationary phase; Enantiomer separation; Liquid chromatography;
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Times Cited By Web Of Science : 14  (Related Records In Web of Science)
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1 Chiral Separation Techniques: A Practical Approach; Subramanian, G., Ed.; Wiley-VCH: Weinheim, 2001
2 Aboul- Enein, H. Y.; Ali, I. Chiral Separations by Liquid Chromatography and Related Technologies; Marcel Dekker: New York, 2003
3 Hyun, M. H. Bull. Kor. Chem. Soc. 2005, 26, 1153   DOI   ScienceOn
4 Hyun, M. H. J. Sep. Sci. 2006, 29, 750   DOI   ScienceOn
5 Shinbo, T.; Yamaguchi, T.; Nishimura, K.; Sugiura, M. J. Chromatogr. 1987, 405, 145   DOI   ScienceOn
6 Shinbo, T.; Yamaguchi, T.; Yanagishita, H.; Kitamoto, D.; Sakaki, K.; Sugiura, M. J. Chromatogr. 1992, 625, 101   DOI   ScienceOn
7 Hyun, M. H.; Han, S. C.; Lipshutz, B. H.; Shin, Y.-J.; Welch, C. J. J. Chromatogr. A 2001, 910, 359   DOI   ScienceOn
8 Hyun, M. H.; Han, S. C.; Lipshutz, B. H.; Shin, Y.-J.; Welch, C. J. J. Chromatogr. A 2002, 959, 7
9 Hyun, M. H.; Cho, Y. J.; Jin, J. S. J. Sep. Sci. 2002, 25, 648   DOI   ScienceOn
10 Hyun, M. H.; Cho, Y. J.; Kim, J. A.; Jin, J. S. J. Liq. Chromatogr. Rel. Technol. 2003, 26, 1083   DOI   ScienceOn
11 Berkecz, R.; Sztojkov-Ivanov, A.; Ilisz, I.; Forro, E.; Fulop, F.; Hyun, M. H.; Peter, A. J. Chromatogr. A 2006, 1125, 138   DOI   ScienceOn
12 Hyun, M. H.; Jin, J. S.; Koo, H. J.; Lee, W. J. Chromatogr. A 1999, 837, 75   DOI   ScienceOn
13 Hyun, M. H.; Jin, J. S.; Lee, W. Bull. Kor. Chem. Soc. 1998, 19, 819
14 Hyun, M. H.; Han, S. C.; Cho, Y. J.; Jin, J. S.; Lee, W. Biomed. Chromatogr. 2002, 16, 356   DOI   ScienceOn
15 Hyun, M. H.; Kim, Y. H.; Cho, Y. J. Bull. Kor. Chem. Soc. 2004, 25, 400   DOI   ScienceOn
16 Hyun, M. H.; Cho, Y. J. J. Sep. Sci. 2005, 28, 31   DOI   ScienceOn
17 Wasserman, H. H.; Matsuyama, H.; Robinson, R. P. Tetrahedron 2002, 58, 7177   DOI   ScienceOn
18 Juaristi, E.; Soloshonok, V. A. Enantioselective Synthesis of $\beta$-Amino Acids, 2nd ed.; Wiley- VCH: New York, 2005
19 Pirkle, W. H.; Koscho, M. E. J. Chromatogr. A 1999, 840, 151   DOI   ScienceOn
20 Hyun, M. H. J. Sep. Sci. 2003, 26, 242   DOI   ScienceOn
21 Hyun, M. H.; Han, S. C.; Jin, J. S.; Lee, W. Chromatographia 2000, 52, 473   DOI   ScienceOn
22 Hyun, M. H.; Min, H. J.; Cho, Y. J. Bull. Kor. Chem. Soc. 2003, 24, 911   DOI   ScienceOn
23 Hyun, M. H.; Jin, J. S.; Lee, W. J. Chromatogr. A 1998, 822, 155   DOI   ScienceOn
24 Hyun, M. H.; Han, S. C. J. Biochem. Biophys. Methods 2002, 54, 235   DOI   ScienceOn
25 Hyun, M. H.; Min, H. J.; Cho, Y. J. J. Chromatogr. A 2003, 996, 233   DOI   ScienceOn
26 Hyun, M. H.; Tan, G.; Cho, Y. J. Biomed. Chromatogr. 2005, 19, 208   DOI   ScienceOn