title: High-performance liquid chromatographic separation of paclitaxel intermediate phenylisoserine derivatives on macrocyclic glycopeptide and cyclofructan-based chiral stationary phases.
abstract: High-performance liquid chromatographic methods were developed for the separation of enantiomers of four unnatural paclitaxel precursor phenylisoserine analogs on chiral stationary phases containing macrocyclic glycopeptides and cyclofructans as chiral selectors. The effects of the mobile phase composition, the nature and concentration of different mobile phase additives (alcohols, amines and acids) in different chromatographic modes, temperature and the structures of the analytes on the separations were investigated. Separations were carried out at constant mobile phase compositions in the temperature range 10-50°C on macrocyclic antibiotic-based and 5-35°C on cyclofructan-based columns and the changes in enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated. The elution sequence was determined in most cases; no general rule could be observed.
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.
authors.forename: István
authors.initials: I
authors.lastname: Ilisz
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary; Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary.
authors.forename: Nóra
authors.initials: N
authors.lastname: Grecsó
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary.
authors.forename: Enikő
authors.initials: E
authors.lastname: Forró
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary.
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
authors.forename: Daniel W
authors.initials: DW
authors.lastname: Armstrong
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.
authors.forename: Antal
authors.initials: A
authors.lastname: Péter
mesh_terms: D000438:Alcohols; D000900:Anti-Bacterial Agents / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D019277:Entropy; D005630:Fructans / Q000737:chemistry*; D006020:Glycopeptides / Q000737:chemistry*; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D017239:Paclitaxel / Q000737:chemistry / Q000302:isolation & purification*; D010455:Peptides / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000900:Anti-Bacterial Agents; D005630:Fructans; D006020:Glycopeptides; D010455:Peptides; D012694:Serine; C010286:beta-phenylisoserine; D017239:Paclitaxel
keywords: Column liquid chromatography; Cyclofructan-based chiral stationary phases; Macrocyclic glycopeptide-based chiral stationary phases; Phenylisoserine analogs