Document Detail


Cellulose tris(3,5-dimethylphenylcarbamate)-based chiral stationary phases as effective tools for enantioselective HPLC separation of structurally different disubstituted binaphthyls.
MedLine Citation:
PMID:  18553496     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
Cellulose tris(3,5-dimethylphenylcarbamate)-based chiral stationary phases (CSPs) were used for a study of the HPLC retention and enantioseparation behavior of 2,2'-disubstituted or 3,2,2'-trisubstituted 1,1'-binaphthyls and 8,3'-disubstituted 1,2'-binaphthyls. The effects of the mobile phase composition in normal- (NP) and reversed-phase (RP) separation modes were investigated. The NP mobile phases contained n-hexane and propane-2-ol at various volume ratios, the RP ones were obtained by mixing acetonitrile with water or a 20 mM phosphate buffer of pH 6.0 or 3.0. The RP separation mode has been found more suitable for enantioresolution of most of the analytes. The best enantioseparation of 2,2'-diacetyl-1,1'-binaphthyl, 2-hydroxy-2'-(phenylamino)-1,1'-binaphthyl-3-carboxylic acid and 2-amino-2'-hydroxy-1,1'-binaphthyl-3-carboxylic acid was obtained in the mobile phase of ACN/20 mM phosphate buffer, pH 3.0, 40/60 (v/v), whereas N-(2'-hydroxy-1,1'-binaphthyl-2-yl)acetamide, N-(3'-methoxy-1,2'-binaphthyl-8-yl)acetamide, and N-(3'-hydroxy-1,2'-binaphthyl-8-yl)acetamide yielded better results in ACN/water at the same v/v ratio. The analyte-CSP interaction mechanism was found to be temperature independent but the enantioresolution improved at an elevated temperature. The mechanism of the enantioselective discrimination is discussed on the basis of the thermodynamic parameters obtained. Semi-preparative separation conditions have been proposed for 2-amino-2'-hydroxy-1,1'-binaphthyl-3-carboxylic acid, N-(3'-methoxy-1,2'-binaphthyl-8-yl)acetamide, and N-(3'-hydroxy-1,2'-binaphthyl-8-yl)acetamide.
Authors:
Lucie Loukotková; Milena Rambousková; Zuzana Bosáková; Eva Tesarová
Related Documents :
15739426 - A novel chiral stationary phase derived from l-proline for liquid chromatographic resol...
19575466 - Simultaneous determination of enantiomerization and hydrolysis kinetic parameters of ch...
17262336 - Hplc analysis of the main furanocoumarins from peucedanum palustre.
19203756 - Simultaneous determination of diastereoisomeric and enantiomeric impurities in sss-octa...
23682846 - Development and characterization of multilamellar liposomes containing pyridostigmine.
22319276 - Galvanostatic entrapment of penicillinase into polytyramine films and its utilization f...
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chirality     Volume:  20     ISSN:  1520-636X     ISO Abbreviation:  Chirality     Publication Date:  2008 Aug 
Date Detail:
Created Date:  2008-07-16     Completed Date:  2008-10-10     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  United States    
Other Details:
Languages:  eng     Pagination:  900-9     Citation Subset:  -    
Copyright Information:
(c) 2008 Wiley-Liss, Inc.
Affiliation:
Faculty of Science, Department of Analytical Chemistry, Charles University in Prague, 128 43 Prague 2, Czech Republic.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  A model predicting delivery of saquinavir in nanoparticles to human monocyte/macrophage (Mo/Mac) cel...
Next Document:  Direct screening of chiral discrimination abilities of chiral hosts using mass spectrometry.