Published:Journal of Chromatographic Science,
ISSN 0021-9665Volume
40, Number 2, February 2002, pp. 83-86
Displacement Study on a Vancomycin-Based Stationary Phase Using
N-acetyl-d-Alanine as a Competing Agent
Ines Slama, Corinne Ravelet,
Annick Villet, Anne Ravel, Catherine Grosset, and Eric Peyrin*
Laboratoire de Chimie Analytique, UFR de Pharmacie de Grenoble, UJF, Domaine de
la Merci, 38700 La Tronche, France
The analysis of the binding data of d,l-dansyl amino acids on
a vancomycin stationary phase is investigated in relation to the addition of
N-acetyl-d-alanine in the mobile phase. This eluent additive acts as a specific
competing agent for the aglycone pocket of the immobilized chiral selector.
A model taking into account both stereoselective and nonstereoselective interactions
between the solutes and the stationary phase is used to fit the experimental
data. From the results, the theoretical approach is considered to be adequate
to describe the competing agent dependence on solute retention. To the best
of our knowledge, this report constitutes the first example of a displacement
study on a macrocyclic antibiotic stationary phase. This work shows that dansyl
amino acids bind to the active aglycone pocket of the selector and that this
interaction is enantioselective. The results also demonstrate that additional
enantioselective sites at the vancomycin surface are involved in the chiral
discrimination of these solutes.
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