Chiral stationary phases for HPLC

Proteias, amino acids bonded through peptide linkages to form macromolecular biopolymers, used as chiral stationary phases for hplc iaclude bovine and human semm albumin, a -acid glycoproteia, ovomucoid, avidin, and ceUobiohydrolase. The bovine semm albumin column is marketed under the name Resolvosil and can be obtained from Phenomenex. The human semm albumin column can be obtained from Alltech Associates, Advanced Separation Technologies, Inc., and J. T. Baker. The a -acid glycoproteia and ceUobiohydrolase can be obtained from Advanced Separation Technologies, Inc. or J. T. Baker, Inc. 

Scheme 2.5. Chiral Stationary Phases for HPLC Separation of Enantiomers...

In addition to the development of the powerful chiral additive, this study also demonstrated that the often tedious deconvolution process can be accelerated using HPLC separation. As a result, only 15 libraries had to be synthesized instead of 64 libraries that would be required for the full-scale deconvolution. A somewhat similar approach also involving HPLC fractionations has recently been demonstrated by Griffey for the deconvolution of libraries screened for biological activity [76]. Although demonstrated only for CE, the cyclic hexapeptides might also be useful selectors for the preparation of chiral stationary phases for HPLC. However, this would require the development of non-trivial additional chemistry to appropriately link the peptide to a porous solid support. 

Armstrong, D.W., Zhang, B. (2001). Chiral stationary phases for HPLC. Anal. Chem. 73, 557A-561A. 

Armstrong, D.W., Liu, Y., and Ekborg-Ott, K.H., A covalently bonded teico-planin chiral stationary phase for HPLC enantioseparations. Chirality, 7, 474, 1995. 

D Acquarica, L, New synthetic strategies for the preparation of novel chiral stationary phases for HPLC containing natural pool selectors, presented at 8 Int. Meeting on Recent Developments in Pharmaceutical Analysis, Roma, June 29-July 3, 1999, 37. 

Yashima, E., Huang, S., and Okamoto, Y. (1994) An optically active stereoregular polyphenylacetylene derivative as a novel chiral stationary phase for HPLC, J. Chem. Soc., Chem. Commun. 1811-1812. 

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. 

Kubota, T., Yamamoto, C., and Okamoto, Y. (2003) Preparation of chiral stationary phase for HPLC based on immobilization of cellulose 3,5-dimethylphenylcarbamate derivatives on silica gel, Chirality 15, 77-82. 

The thermodynamic and hydrogen-bond basicity of 1 have been reported by the group of Berthelot, Laurence and coworkers (04CJC1413). TB 1, TB 110 and another mixed crown ether TB have been reported in a communication dealing with a novel chiral stationary phase for HPLC (94JCS(CC)1811). 

Chiral Stationary Phases for HPLC Name Bovine serum albumin (covalently fixed to silica gel)... 

Kubota,T, Kusano,T, Yamamoto, C., Yashima, E., Okamoto, Y. Cellulose 3,5-dimethylphenylcarbamate immobilized onto silica gel via copolymerization with a vinyl monomer and its chiral recognition ability as a chiral stationary phase for HPLC, Chem. Lett., 2001, 724-725. 

TABLE 22.1 Some chiral stationary phases for HPLC ... 

Chromatographic evaluation of poly (trans 1,2-cyclohexanediyl-bis-acrylamide) as a chiral stationary phase for HPLC.J. Chromatogr. A, 1066, 55-70. 

D. W. Armstrong, Y. Liu and K. H. Ekborgott, A Covalently Bonded Teicoplanin Chiral Stationary Phase for HPLC Enantioseparations, Chirality, 7(1995)474. 

N. Oi, Recent progress of chiral stationary phases for HPLC, in Advances in Liquid Chromatography, ed. T. Hanai and H. Hatano, World Scientific, Singapore, 1996, pp. 213-230. 

Self-assembled structures are supramolecular assemblies of covalent backbones structured through intra- and interchain noncovalent interactions. These secondary structures arise from steric constraints and a network of weak interactions (i.e., hydrogen or Van der Waals bonding, dipole-dipole or amphiphilic interactions). Helical morphologies are stiU rarely represented in these artificial species but the control of the heHx sense, and a better knowledge of the chiral amplification mechanism, is highly desirable due to their potential use in many applications. For example, helically chiral polymers can be used as chiral stationary phases for HPLC or for catalysis. 

Development of chiral stationary phases for HPLC separations of enantiomeric mixtures is a highly active field. A useful review (Dappen 1986) covers earlier work, and more recent overviews (Beesley 2004 Bojarski 2005) of such developments are supplemented by a review of chiral LC/MS quantitation in the pharmaceutical industry (Chen 2005). Chiral stationary phases have specific requirements concerning mobile phases and this raises nontrivial questions concerning the ionization technique (Chapter 5) that is best suited to interfacing with a mass spectrometer in any particular case. 

---