Enantiomeric Separation of Aromatic Amino Alcohol Drugs By Chiral Ion-Pair Chromatography On A Silica Gel Plate

Huang, M. B.; Li, Gao-Lan; Yang, Guangming; Shi, Yuhao; Gao, Jianjun; Liu, Xiang-De

doi:10.1080/10826079708010990

Cited by 19 publications

(4 citation statements)

References 9 publications

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“…A similar strong effect of the solvent on the operational selectivity was described by Huang et al 37 for a TLC/CMP separation. Other model enantiomers were tested with both OH-C 12 Hyp/Cu(II) and C 12 Hyp/Cu(II) using butanol/hexane solvent mixtures with high hexane content (75 or 83 vol%), under the same circumstances as for the norephedrine separation.…”

Section: Performance Of Selective Candidate Extractant Systemssupporting

confidence: 71%

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Identification of enantioselective extractants for chiral separation of amines and aminoalcohols

et al. 2006

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The major obstacle for the introduction of fractional reactive extraction as a chiral separation method in the chemical and pharmaceutical industries is the lack of versatile enantioselective extractants. Therefore, a rational approach is developed to transfer the extensive knowledge of chiral selectors reported in the literature on chiral recognition and other chiral separation techniques to extraction. Based on a similarity in separation mechanisms, it was expected that chiral selectors originating from a technique in which chiral recognition takes place in the liquid phase are most likely to function as enantioselective extractant. Using this approach, a selection of promising extractants was made from the literature and experimentally evaluated for the enantioseparation of aminoalcohols and amines. As a result, four enantioselective extractant systems, namely, dibutyl-L-tartrate with boric acid, N-(2-hydroxydodecyl)-L-hydroxyproline Cu(II) complex, N-dodecyl-L-hydroxyproline Cu(II) complex, and azophenolic crown ether, have been identified. The azophenolic crown ether system performed the best and demonstrated an enantioselectivity between 1.3-5.0 for five out of six test compounds. Identification of the enantioselective extractant systems was highly facilitated by the developed rational transfer approach that, although partially qualitative, appeared capable of reducing more than 50 encountered candidates to only three promising systems for further experimental evaluation. Therefore, it is expected that this approach can be successfully applied to identify enantioselective extractants for other classes of enantiomers as well.

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Section: Performance Of Selective Candidate Extractant Systemssupporting

confidence: 71%

“…For instance, in the TLC/CMP measurements by Huang et al, 37 using camphorsulphonate as chiral selector for beta-blockers, the temperature and the solvent composition were crucial to obtain chiral separation.…”

Section: Selection Of Candidate Enantioselective Extractants For Aminmentioning

confidence: 99%

Identification of enantioselective extractants for chiral separation of amines and aminoalcohols

et al. 2006

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“…Separation of enantiomers of β-blockers has also been achieved on TLC plates impregnated with ammonium-D-10-camphor sulfonate (Huang et al, 1997), on LiChrosorb Diol highperformance TLC plates with dichloromethane and a chiral counter ion, N-benzyloxycarbonylglycyl-L-proline, as mobile phase additive (Tivert and Beckman, 1993), and by use of a molecularly imprinted polymer (Suedee et al, 1999(Suedee et al, , 2001). Direct resolution of a variety of compounds on impregnated TLC plates has been reported by Bhushan and Martens (1997, 2007.…”

Section: Introductionmentioning

confidence: 99%

Direct TLC resolution of atenolol and propranolol into their enantiomers using three different chiral selectors as impregnating reagents

Bhushan

Tanwar

2008

Biomedical Chromatography

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Direct resolution of racemic atenolol and propranolol into their enantiomers was achieved by normal phase TLC on silica gel plates impregnated with optically pure L-tartaric acid, (R)-mandelic acid and (-)-erythromycin as chiral selectors. Different solvent systems were worked out to resolve the enantiomers. Spots were detected using iodine vapour. The TLC method was validated for linearity, limit of detection and limit of quantification. The influence of pH, temperature and concentration of chiral selector was studied.

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“…A literature survey reveals a lot of analytical methods for the determination of propranolol in pharmaceuticals and in biological fluids. The more recent articles are concerned with the analysis of propranolol and include different techniques, UV spectroscopy [12], colorimetry [13], thin layer chromatography for enantiomer separation [14], HPLC in biological fluids [15], cation Exchange HPLC in spiked plasma [16], micellar liquid chromatography in urine samples [17] and electrochemical methods [18]. In our previous article, we synthesized and characterized Cu(II) and Co(II) complexes of propranolol too [19].…”

Section: Introductionmentioning

confidence: 99%

Transition Metal Complexes of Propranolol Dithiocarbamate: Synthesis, Characterization, Analytical Properties and Biological Activity

Gölcü

2006

Transition Met Chem

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Propranolol dithiocarbamate (PDTC) and its complexes with Cu(II), Co(II), Ni(II), Zn(II) and Cd(II) have been synthesized and characterized by elemental analyses, FT-IR, electronic spectra, atomic absorption spectra, molar conductance, mass and 1 H-n.m.r. spectral data. Information on the stoichiometry of the complexes was obtained from the continuous variation method (Job's method). The thermal decomposition behaviour of PDTC metal complexes was investigated in a nitrogen atmosphere using TG and DTA techniques. The antimicrobial activity studies of the metal complexes have been recorded against the Bacillus megaterium, Bacillus brevis, Yersinia enterocolitica, Micrococcus luteus, Pseudomonas aeruginosa, Enterococcus faecalis, Kluyveromyces marxianus, Candida tropicalis, Candida albicans and Kluvyeromyces fragilis.

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Enantiomeric Separation of Aromatic Amino Alcohol Drugs By Chiral Ion-Pair Chromatography On A Silica Gel Plate

Cited by 19 publications

References 9 publications

Identification of enantioselective extractants for chiral separation of amines and aminoalcohols

Identification of enantioselective extractants for chiral separation of amines and aminoalcohols

Direct TLC resolution of atenolol and propranolol into their enantiomers using three different chiral selectors as impregnating reagents

Transition Metal Complexes of Propranolol Dithiocarbamate: Synthesis, Characterization, Analytical Properties and Biological Activity

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