A new isothiocyanato-type CDA, (R,R)- or (S,S)-DANI, was designed for the indirect HPLC enantioseparation of primary and secondary amino compounds. The new reagent is readily available in enantiomerically pure form (≥99,5%) after a straightforward two-step synthesis. It is stable chemically and stereochemically both in the solid and in the solution phase. It is available in both enantiomeric forms, allowing the appropriate selection of the elution sequence. The kinetics of derivatization was studied in detail for α-amino acids. By optimizing the reaction conditions (pH, reagent excess, temperature), the quantitativeness of derivatizations was ensured. As concerns the HPLC analyses of the thiourea derivatives formed, significant differences were found between the selectivities of the organic modifiers applied; in most cases, MeOH proved much more effective than MeCN with respect to both retention times and resolutions. The sequence of elution of the diastereomers was studied, but no general rule could be found. In conclusion, the new CDA was capable of the resolution of most of the investigated analytes.
|Translated title of the contribution||Synthesis and application of a new chiral derivatizing agent to the liquid chromatographic enantioseparation of amino compounds|
|Number of pages||12|
|Journal||Magyar Kemiai Folyoirat, Kemiai Kozlemenyek|
|Publication status||Published - Apr 1 2002|
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