Novel cinchona alkaloid O9-hydrazide derivatives as chiral anion-exchange-type selectors: Synthesis and chromatographic evaluation

  title={Novel cinchona alkaloid O9-hydrazide derivatives as chiral anion-exchange-type selectors: Synthesis and chromatographic evaluation},
  author={Pilar Franco and Michael L{\"a}mmerhofer and P M Klaus and Wolfgang Lindner},
SummarySix new quinine (QN) O9-hydrazide derivatives with different substituents have been synthesized and immobilized on porous silica gel for HPLC. The chiral resolving power of these anion-exchange-type chiral stationary phases (CSPs) has been investigated and compared with that of four carbamate QN derivatives with analogous substitution. The unsubstituted QN-hydrazide derivative was usually the best chiral selector of the hydrazide series. Among the substituted hydrazide derivatives the… 
Structure‐enantioselectivity relationships for the study of chiral recognition in peptide enantiomer separation on cinchona alkaloid‐based chiral stationary phases by HPLC: Influence of the N‐terminal protecting group
Eleven different N-terminal protecting groups (acetyl, benzoyl, FMOC, etc.) were employed for the HPLC separation of oligoalanine peptide enantiomers containing up to six amino acids. Isocratic HPLC
Evaluation of the contribution to enantioselectivity of quinine and quinidine scaffolds in chemically and physically mixed chiral selectors.
Three "dimeric" C(9)-carbamates of quinine (QN) and quinidine (QD) were synthesized and used as chiral selectors for HPLC and capillary electrophoresis (CE) for the resolution of chiral acids.
Comparative molecular field analysis of quinine derivatives used as chiral selectors in liquid chromatography: 3D QSAR for the purposes of molecular design of chiral stationary phases.
A comparative molecular field analysis was carried out on a set of aligned quinine-based stationary phase molecules used in enantioselective chromatography, and it was concluded that the long-range electrostatic potential surrounding the positively charged CSPs are not enantiodiscriminating, while the van der Waals and local electrostatic surface features of these C SPs are highly discriminating.
Precolumn derivatization of reducing carbohydrates with 4-(3-Methyl-5-oxo-2-pyrazolin-1-yl) benzoic acid. Study of reaction, high-performance liquid chromatographic separation and quantitative performance of method
SummaryA simple method for quantitative determination of carbohydrates by reversed-phase, high-performance liquid chromatography after pre-column derivatization and UV detection has been developed.
Chiral Stationary Phases Based on Small Molecules: An Update of the Last 17 Years
A literature survey covering the report on Pirkle-type chiral stationary phases (CSPs) from January 2000 to March 2017 is presented in this review. More than 200 CSPs comprising small molecules as
Quinine conjugates and quinine analogues as potential antimalarial agents.


Enantioselective anion exchangers based on cinchona alkaloid-derived carbamates: influence of C8/C9 stereochemistry on chiral recognition.
The enantioseparation potential of quinine- and quinidine-derived CSPs proved to be far superior to that of their C9-epimeric congeners, and the absolute configuration of C9 stereogenic center of the cinchonan backbone of these selectors was identified as the structural feature controlling the elution order.
High‐performance liquid chromatographic enantioseparation of N‐protected α‐amino acids using nonporous silica modified by a quinine carbamate as chiral stationary phase
In this study, tert-butyl carbamoylated quinine as chiral selector was immobilized on nonporous silica (NPS) 1.5 μm particles developed by MICRA, and this new chiral stationary phase (CSP) was packed