Abstract
Chiral separation by high-performance liquid chromatography (HPLC) using a chiral stationary phase (CSP) is one of the most efficient methods for separating enantiomers, not only on an analytical scale, but also on a preparative scale, and in the past two decades, many CSPs have been developed. Polysaccharides such as cellulose, amylose, and chitin (Fig. 1) are the most abundant optically active polymers on the earth and can be readily modified to carbamates and esters through the reaction with isocyanates and acid chlorides, respectively. The CSPs based on polysaccharide derivatives are some of the most popular ones and can separate a wide range of chiral compounds (1–4).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Okamoto, Y. and Kaida, Y. (1994) Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phases. J. Chromatogr. A 666, 403–419.
Yashima, E. and Okamoto, Y. (1995) Chiral discrimination on polysaccharides derivatives. Bull. Chem. Soc. Jpn. 68, 3289–3307.
Okamoto, Y. and Yashima, E. (1998) Polysaccharide derivatives for chromatographic separation of enantiomers. Angew. Chem. Int. Ed. 37, 1020–1043.
Yashima, E., Yamamoto, C., and Okamoto, Y. (1998) Polysaccharide-based chiral LC columns. Synlett 344–360.
Okamoto, Y., Kawashima, M., Yamamoto, K., and Hatada, K. (1984) Useful chiral packing materials for high-performance liquid chromatographic resolution. Cellulose triacetate and tribenzoate coated on macroporous silica gel. Chem. Lett. 739–742.
Ichida, A., Shibata, T., Okamoto, I., Yuki, Y., Namikoshi, H., and Toda, Y. (1984) Resolution of enantiomers by HPLC on cellulose derivatives. Chromatographia 19, 280–284.
Okamoto, Y., Aburatani, R., and Hatada, K. (1987) Cellulose tribenzoate derivatives as chiral stationary phases for high-performance liquid chromatography. J. Chromatogr. 389, 95–102.
Okamoto, Y., Kawashima, M., and Hatada, K. (1986) Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel. J. Chromatogr. 363, 173–186.
Chankvetadze, B., Yamamoto, C., and Okamoto, Y. (2000) Extremely high enantiomer recognition in HPLC separation of racemic 2-(benzylsulfinyl)benzamide using cellulose tris(3,5-dichlorophenylcarbamate) as a chiral stationary phase. Chem. Lett. 67–77.
Kubota, T., Yamamoto, C., and Okamoto, Y. (2000) Tris(cyclohexylcarbamate)s of cellulose and amylose as potential chiral stationary phases for high-performance liquid chromatography and thin-layer chromatography. J. Am. Chem. Soc. 122, 4056–4059.
Okamoto, Y., Aburatani, R., Fukumoto, T., and Hatada, K. (1987) Useful chiral stationary phases for HPLC. Amylose tris(3,5-dimethylphenylcarbamate) and tris(3,5-dichlorophenylcarbamate) supported on silica gel. Chem. Lett. 1857–1860.
Yashima, E., Kasashima, E., and Okamoto, Y. (1997) Enantioseparation on 4-halogen-substituted phenylcarbamates of amylose as chiral stationary phases for high-performance liquid chromatography. Chirality 9, 63–68.
Okamoto, Y., Kaida, Y., Hayashida, H., and Hatada, K. (1990) Tris(1-phenylethyl-carbamate)s of cellulose and amylose as useful chiral stationary phases for chromatographic optical resolution. Chem. Lett. 909–912.
Yamamoto, C., Hayashi, T., Okamoto, Y., and Kobayashi, S. (2000) Enantioseparation by using chitin phenylcarbamates as chiral stationary phases for high-performance liquid chromatography. Chem. Lett. 12–13.
Ishikawa, A. and Shibata, T. (1993) Cellulosic chiral stationary phase under reversed-phase condition. J. Liq. Chromatogr. 16, 859–878.
Tachibana, K. and Ohnishi, A. (2001) Reversed-phase liquid chromatographic separation of enantiomers on polysaccharide type chiral stationary phases. J. Chromatogr. A 906, 127–154.
Shibata, T., Okamoto, I., and Ishii, K. (1986) Chromatographic optical resolution on polysaccharides and their derivatives. J. Liq. Chromatogr. 9, 313–340.
Dingene, J. (1994) Polysaccharide phases in enantioseparations, in A Practical Approach to Chiral Separations by Liquid Chromatography (Subramanian, G., ed.), VCH, New York, pp. 115–181.
Maeda, K., Okamoto, Y., Toledano, O., Becker, D., Biali, S. E., and Rappoport, Z. (1994) Multiple buttressing interactions: enantiomerization barrier of tetrakis(pentamethylphenyl)ethane. J. Org. Chem. 59, 5473–5475.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2004 Humana Press Inc.,Totowa, NJ
About this protocol
Cite this protocol
Yamamoto, C., Okamoto, Y. (2004). Chiral Separation by HPLC Using Polysaccharide-Based Chiral Stationary Phases. In: Gübitz, G., Schmid, M.G. (eds) Chiral Separations. Methods in Molecular Biology, vol 243. Humana Press. https://doi.org/10.1385/1-59259-648-7:173
Download citation
DOI: https://doi.org/10.1385/1-59259-648-7:173
Publisher Name: Humana Press
Print ISBN: 978-1-58829-150-9
Online ISBN: 978-1-59259-648-5
eBook Packages: Springer Protocols