Enantioseparation of amino alcohols by reversed-phase high-performance liquid chromatography using cyanuric chloride-based chiral derivatizing reagents having amino acids and their amides as chiral auxiliaries

Czasopismo : Acta Chromatographica
Tytuł artykułu : Enantioseparation of amino alcohols by reversed-phase high-performance liquid chromatography using cyanuric chloride-based chiral derivatizing reagents having amino acids and their amides as chiral auxiliaries

Autorzy :
Fatemi, M. H.
University of Mazandaran Faculty of Chemistry Babolsar Iran,
Hadjmohammadi, M. R.
University of Mazandaran Faculty of Chemistry Babolsar Iran, hdjmr@umz.ac.ir,
Shakeri, P.
University of Mazandaran Faculty of Chemistry Babolsar Iran,
Bhushan, R.
Indian Institute of Technology Roorkee Department of Chemistry Roorkee 247667 India, rbushfcy@iitr.ernet.in,
Lal, M.
Indian Institute of Technology Roorkee Department of Chemistry Roorkee 247667 India,
Abstrakty : A high-performance liquid chromatographic (HPLC) method was developed for enantioresolution of amino alcohols using an indirect approach. Two sets of chiral derivatizing reagents (CDRs) having amino acids (CDRs 1–4; set A) and their amides (CDRs 5–8; set B) as chiral auxiliaries in cyanuric chloride (CC) moiety were synthesized and characterized. Diastereomers of eight amino alcohols were synthesized, under microwave irradiation, using each of the eight CDRs. The resulting diastereomers were separated by reversed-phase high-performance liquid chromatography (RP-HPLC) using C18 column and eluting mixtures of acetonitrile with aqueous trifluoroacetic acid (aq.TFA) in a linear gradient (45 min) with UV detection at 230 nm. The results (in terms of resolution Rs and retention factor k) obtained for the two sets of diastereomers were compared among themselves and among the two groups. The effects of chiral auxiliaries (in terms of acid and amides variants), constituting CDRs, on separation were also evaluated. The elution order for the diastereomers was determined. The separation method was validated for limit of detection (LOD), linearity, accuracy, precision, and recovery.

Słowa kluczowe : enantioseparation, amino alcohols, reversed-phase high-performance liquid chromatography, cyanuric chloride, chiral derivatizing reagents, microwave irradiation,
Wydawnictwo : University of Silesia in Katowice
Rocznik : 2014
Numer : Vol. 26, no. 3
Strony : 413 – 427
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DOI :
Cytuj : Fatemi, M. H. ,Hadjmohammadi, M. R. ,Shakeri, P. ,Bhushan, R. ,Lal, M. , Enantioseparation of amino alcohols by reversed-phase high-performance liquid chromatography using cyanuric chloride-based chiral derivatizing reagents having amino acids and their amides as chiral auxiliaries. Acta Chromatographica Vol. 26, no. 3/2014
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