A Chromatographic Approach to Analyze Dansyl Amino Acid–HP-b-CD Association Using Macrocyclic Antibiotic as the Stationary Phase

Published: Journal of Chromatographic Science, ISSN 0021-9665 Volume 41, Number 6, July 2003, pp. 311-316

C. André[1], M. Thomassin[1], T.T. Truong[1], J.F. Robert[2], and Y.C. Guillaume[1]
[1]Laboratoire de Chimie Analytique and
[2]Chimie Organique et Thérapeutique, Faculté de Médecine et de Pharmacie, Place Saint-Jacques, 25030 Besançon cedex, France

The retention mechanism for a series of d,l-dansyl amino acids in high-performance liquid chromatography is investigated using a teicoplanin stationary phase and hydroxypropyl-b-cyclodextrin (HP-b-CD) as the mobile phase additive (0–16mM). A theoretical treatment is developed to determine the HP-b-CD influence on the equilibrium between the teicoplanin phase and the aqueous medium, respectively. From the experimental data, the association constants of the d,l-dansyl amino acids–HP-b-CD inclusion complexes are determined and discussed in relation to the enantiomer structure. A thermodynamic study confirms that both the retention and complexation mechanisms are independent of the dansyl amino acid molecular structure and its absolute carbon configuration.

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