This article describes our attempt to re-visit the role of temperature in the separation of enantiomers with polysaccharide-based chiral columns in high-performance liquid chromatography (HPLC). Rarely observed increased retention and separation factors with increasing temperature, as well as temperature dependent reversal of enantiomer elution order are reported for several arylpropionic acid derivatives. Chiral columns with coated and covalently immobilized chiral selectors were compared from the viewpoint of effect of temperature on analyte retention, enantiomer separation and enantiomer elution order. Thermodynamic parameters were calculated for analyte transfer from the liquid phase to the chiral stationary phase and the effect of temperature on chiral selectors was investigated by using differential scanning calorimetry (DSC). DSC results along with chromatographic studies indicate that polysaccharide-based chiral selectors undergo some kind of transition at elevated temperature that is not reversible in the thermodynamic sense of this term.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.chroma.2019.04.024 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
First separation of commendamide enantiomers.
J Pharm Biomed Anal
December 2024
Institute of Biomolecular Chemistry ICB, CNR, Traversa La Crucca 3, Regione Baldinca, Li Punti, Sassari 07100, Italy. Electronic address:
N-(3-hydroxyacyl)glycines are compounds of remarkable interest due to their biogenic origin and bioactivity and as precursors of the corresponding 3-acyloxy derivatives which represent an important class of bioactive products of bacterial origin. Commendamide [N-(3-hydroxypalmitoyl)glycine] (1) is a gut microbiota-derived bioactive metabolite that is structurally like endogenous long-chain N-acyl-amino acids belonging to the endocannabinoidome, a complex lipid signaling system involved in several aspects of mammalian physiology and pathology. Thanks to this structural similarity, this compound and its analogues, like the N-(3-hydroxymyristoyl)glycine 2, exert a remarkable bioactivity in mammals, for instance, through activation of G-protein-coupled receptors (GPCRs).
View Article and Find Full Text PDFSupercritical fluid chromatography for milligram preparation of enantiomers.
Biomed Chromatogr
January 2025
Univ. Lille, Inserm, Lille, France.
Article Synopsis
- Preparative chromatographic enantioseparation is the top method for isolating pure enantiomers during the early development of new drugs.
- Supercritical fluid chromatography was chosen for this process due to its advantages over traditional liquid chromatography.
- A total of 10 mg of each enantiomer of a new anti-inflammatory compound was successfully isolated, although some peak distortion occurred during testing, likely caused by the method of injection used.
Possibilities and limitations of computer assisted chiral HPLC method development for ozanimod on polysaccharide based chiral stationary phases.
Sci Rep
November 2024
Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes E. u. 9, Budapest, 1092, Hungary.
In this study, a direct HPLC method was developed to determine the enantiomeric purity of the immunomodulatory drug, ozanimod. A systematic method development process was followed, incorporating risk assessment, identification of critical analytical procedure parameters, initial screening of stationary phases, and software-assisted optimization of method parameters. Eight different polysaccharide-based chiral columns were selected to assess chiral separation of enantiomers under polar organic elution mode.
View Article and Find Full Text PDFEvaluation of various polysaccharide-based stationary phases for enantioseparation of chloro-containing derivatives in normal phase liquid chromatography.
Biomed Chromatogr
December 2024
Univ. Lille, Inserm, RID-AGE U1167, Lille, France.
Six polysaccharide-based chiral stationary phases were screened to separate the enantiomers of six chloro-containing derivatives and one derivative bearing electron donating mesomeric substituents, chosen for comparison. These compounds are expected to be P2X7 receptor antagonists with potential anti-inflammatory activity. The study was carried out with four different mobile phases composed of n-heptane and ethanol or isopropanol.
View Article and Find Full Text PDFUnravelling dispersion forces in liquid-phase enantioseparation. Part II: Planar chiral 1-(iodoethynyl)-3-arylferrocenes.
Anal Chim Acta
October 2024
Istituto di Chimica Biomolecolare ICB-CNR, Sede secondaria di Sassari, Traversa La Crucca 3, Regione Baldinca, Li Punti, 07100, Sassari, Italy. Electronic address:
Background: In the first part of our study on possible contribution of dispersion forces in liquid-phase enantioseparations, the enantioseparation of the axially chiral 3,3'-dibromo-5,5'-bis-ferrocenylethynyl-4,4'-bipyridine with an amylose tris(3,5-dimethylphenylcarbamate)-based chiral column appeared reasonably consistent with a picture of the enantioselective recognition based on the interplay between hydrogen bond (HB), π-π stacking and dispersion interactions.
Results: In the second part of this study, we evaluated the impact of analyte and chiral stationary phase (CSP) structure, mobile phase and temperature on the enantioseparations of planar chiral 1-(iodoethynyl)-3-arylferrocenes (3-aryl = phenyl, 2-naphthyl, 4-methylphenyl, 4-t-butylphenyl) with polysaccharide-based chiral columns. The main aim of the present study was to understand the molecular bases of the high affinity observed for the second eluted (R)-enantiomer of some of these analytes toward amylose phenylcarbamate-based selectors when methanol-containing mixtures were used as mobile phases.
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!