Summary
Reversed (RP-HPLC) and normal phase chromatographic (NP-HPLC) separations have been developed for diastereomers ofN-acyl-1-methyl-1,2,3,4-tetrahydo-β-carbolines which are acylated derivatives of simple natural β-carboline alkaloids. Separations of derivatives having different acyl moieties in theO,O-diacyl-tartaric acid ester subtituent differed remarkably. Little or no resolution in either NP-HPLC or RP-HPLC could be achieved with the diacetyl-tartrate derivative. Base-line separation by RP-HPLC but no separation by NP-HPLC was possible with the bulkier and more apolar dipivaloyl derivative. Retention order of the bis-benzoylated diastereomers was reversed and separation time increased dramatically by RP-HPLC. Good separation of the medium polarity, but rigid,N-camphanyl derivative by NP-HPLC has been achieved, whereas RP-HPLC could not be used for separation of these diastereomers. Separability of different diastereomers was highly dependent on polarity and rigidity of the derivatizingN-acyl moieties. Conformational analysis by molecular mechanics and comparison of the lowest energy conformational states of the diastereomers was applied to rationalise separation-retention behaviour of stereoisomers by RP-HPLC.
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Salo, M.; Siren, H.; Volin, P.; Wiedmer, S.; Vuorela, H.J. Chromatogr. A 1996,728, 83–8.
Szepesi, G.; Valkó, K.J. Chromatogr. A 1991,550, 87–100.
Kaliszan, R.J. Chromatogr. A 1993,656, 417–435.
Ho, B.T.; McIsaac, W.M.; Walker, K.E.; Estevez, V.J. Pharm. Sci. 1986,57, 269–274.
Czarnocki, Z.; MacLean, D.B.; Szarek, W.A.Can. J. Chem. 1986,64, 2205–2210.
Czarnocki, Z.; MacLean, D.B.; Szarek, W.A.Bull. Soc. Chim. Belg. 1986,95, 749–770.
Allen, J.R.F.; Holmstedt, B.R.Phytochemistry 1980,19, 1573–1582.
Palamareva, M.D.; Haimova, M.; Stefanovsky, J., Viteva, L.; Kurtev, B.J.J. Chromatogr. 1971,54, 383–391.
Palamareva, M.D.; Kurtev, B.J.J. Chromatogr. 1977,132, 61–72.
Palamareva, M.D.; Kurtev, B.J.J. Chromatogr. 1977,132, 73–82.
Snyder, L.R..Principles of Adsorption Chromatography, Marcel Dekker, New York,1968.
Görög, S.; Gazdag, M.J. Chromatogr B. 1994,659, 51–84.
Toyooka, T.; Liu, Z.-M.; Hanioka, N.; Jinno, H.; Ando, M.; Jimai, K.J. Chromatogr. A 1994,675, 79–88.
Pugniere, M.; Mattras, H.; Castro, B.; Previero, A.J. Chromatogr. A 1997,767, 69–75.
Lanchote, V.L.; Bonato, P.S.; Preossi, S.A.C.; Goncalues, P.V.B.; Cesarino, E.J.; Bertucci, C.J. Chromatogr. B,1996,685, 281–289.
Blaskó, G.; Honty, K.; Novák, L.; Szántay, Cs.Acta Chim. Acad. Sci. Hung. 1979,99, 35–41.
Lucas, H.J.; Baumgarten, W.J. Am. Chem. Soc. 1941,63, 1653–1657.
Butler, C.L.; Cretcher, L.H.J. Am. Chem. Soc. 1933,55, 2605–2606.
Duhamel, L.; Herman, T.; Angiband, P.Synth. Commun. 1992,22, 735–740.
Cuesta, J.; Arsequell, G.; Valencia, G.; Gonzales, A.Tetrahedron Asymmetry 1999,10, 2643–2646.
Calmes, M.; Daunis, J.; Jacquier, R.; Verducci, J.Tetrahedron 1987,43, 2285–2292.
Hyung Ho, H.; Seung-Ryul, H.; Jae-Jeong, R.Chem. Lett. 1994, 1021–1024.
Czarnocki, Z.; MacLean, D.B.; Szarek, W.A.Heterocycles 1992,34, 943–953.
Calter, M.; Hollis, T.K.; Overman, L.E.; Ziller, J.; Zipp, G.G.J. Org. Chem. 1997,62, 1449–1456.
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Fekete, J., Milen, M., Hazai, L. et al. Comparative study on separation of diastereomers by HPLC. Chromatographia 57, 147–153 (2003). https://doi.org/10.1007/BF02491708
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DOI: https://doi.org/10.1007/BF02491708