High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on macrocyclic glycopeptide-based chiral stationary phases.
Summary of "High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on macrocyclic glycopeptide-based chiral stationary phases."
The enantiomers of four unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids were directly separated on chiral stationary phases containing macrocyclic glycopeptide antibiotics teicoplanin (Astec Chirobiotic T and T2), teicoplanin aglycone (Chirobiotic TAG), vancomycin (Chirobiotic V) and vancomycin aglycone (Chirobiotic VAG) as chiral selectors. The effects of the mobile phase composition, the structure of the analytes and temperature on the separations were investigated. Experiments were performed at constant mobile phase compositions in the temperature range 5-45°C to study the effects of temperature, and thermodynamic parameters were calculated from plots of lnk or lnα versus 1/T. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes. It was found that the enantiomeric separations were in most cases enthalpy-driven. The sequence of elution of the enantiomers was determined in all cases.
Affiliation
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary.
Journal Details
This article was published in the following journal.
Name: Journal of chromatography. A
ISSN: 1873-3778
Pages: 142-51
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22177724
- DOI: http://dx.doi.org/10.1016/j.chroma.2011.11.027
Medical and Biotech [MESH] Definitions
Chromatography, High Pressure Liquid
Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed.
Chromatography, Liquid
Chromatographic techniques in which the mobile phase is a liquid.
Child, Gifted
A child or adolescent who, when compared to others of the same age or experience, exhibits capability of high performance in intellectual, creative, or artistic areas, possesses an unusual capacity for leadership or excels in specific academic fields. (From PL 100-297, Sec. 4103, Definitions)
Pyrroloiminoquinones
Derivatives of QUINOLINES with fused PYRROLES and a keto group or INDOLEQUINONES with fused PIPERIDINES.
Azulenes
Compounds based on a seven-membered ring fused to a five-membered ring. Heat can rearrange them to NAPHTHALENES which have two fused six-membered rings. They are similar to guaiazulenes which are SESQUITERPENES with a six-membered ring fused to a five-membered ring.
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