Abstract
Two ligand exchange chiral stationary phases (CSPs) based on (S)-leucinol derivative, sodium N-((S)-1-hydroxymethyl-3-methylbutyl)-N-undecylaminoacetate, and (R)-phenylglycinol derivative, sodium N-((R)-2-hydroxy-1-phenylethyl)-N-undecylaminoacetate, covalently bonded to silica gel have been successfully applied in the resolution of nine α-hydroxycarboxylic acids. The latter was more effective than the former, the separation factors (α) being 1.05 to 2.12 while the resolution factors (RS) varying from 0.18 to 5.29 on the latter. The chromatographic resolution behaviors were dependent on the type and the content of organic modifier and the content of CuSO4 in aqueous mobile phase and the column temperature. A possible chiral recognition mechanism was also proposed based on the chromatographic resolution behaviors.
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References
Davankov VA (2000) Enantiomer 5:209–223
Kurganov A (2001) J Chromatogr A 906:51–71
Davankov VA (2003) J Chromatogr A 1000:891–915
Hyun MH, Ryoo J-J (1996) J Liq Chromatogr Rel Technol 19:2635–2648
Hyun MH, Han SC, Lee CW, Lee YK (2002) J Chromatogr A 950:55–63
Hyun MH, Han SC, Whangbo SH (2003) J Chromatogr A 992:47–56
Hyun MH, Han SC, Whangbo SH (2003) Biomed Chromatogr 17:292–296
Hyun MH, Whangbo SH, Cho YJ (2003) J Sep Sci 26:1615–1622
Coppola GM, Schuster HF (1997) α-Hydroxy acids in enantioselective synthesis. Wiley-VCH, Weinheim
Hor K, Gimple O, Schreier P, Humpf H-U (1998) J Org Chem 63:322–325
Pansare SV, Ravi RG, Jain RP (1998) J Org Chem 63:4120–4124
Chang J-W, Jang J-P, Uang B-J, Liao F-L, Wang S-L (1999) Org Lett 1:2061–2063
Ahuja S (2000) Chiral separations by chromatography. American Chemical Society, Washington, D.C. Oxford University Press
Gubitz G, Mihellyes S (1984) Chromatographia 19:257–259
Gubitz G (1986) J Liq Chromatogr 9:519–535
Yuki Y, Saigo K, Kimoto H, Tachibana K, Hasegawa M (1987) J Chromatogr 400:65–75
Katoh H, Ishida T, Kuwata S, Kiniwa H (1989) Chromatographia 28:481–486
Oi N, Kitahara H, Kira R (1992) J Chromatogr 592:291–296
Gubitz G, Mihellyes S, Kobinger G, Wutte A (1994) J Chromatogr A 666:91–97
Oi N, Kitahara H, Aoki F (1994) J Chromatogr A 666:457–462
Chilmonczyk Z, Ksycinska H, Cybulski J, Rydzewski M, Les A (1998) Chirality 10:821–830
Li S, Purdy WC (1992) J Chromatogr 625:109–120
Okamoto Y, Aburatani R, Kaida Y, Hatada K (1988) Chem Lett 1125–1128
Andrisano V, Booth TD, Cavrini V, Wainer IW (1997) Chirality 9:178–183
Ekborg-Ott K, Liu Y, Armstrong DW (1998) Chirality 10:434–483
Tan L, Chen C-y, Chen W, Frey L, King AO, Tillyer RD, Xu F, Zhao D, Grabowski EJJ, Reider PJ, O’Shea P, Dagneau P, Wang X (2002) Tetrahedron 58:7403–7410
Li W-R, Ewing WR, Harris BD, Joullie MM (1990) J Am Chem Soc 112:7659–7672
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Hyun, M., Kim, J., Cho, Y. et al. Liquid Chromatographic Resolution of Racemic α-Hydroxycarboxylic Acids on Ligand Exchange Chiral Stationary Phases. Chromatographia 60, 275–280 (2004). https://doi.org/10.1365/s10337-004-0358-x
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DOI: https://doi.org/10.1365/s10337-004-0358-x