28
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Thermodynamic Study of Enantioseparation of Arylpropionic Acids with a Chiralcel OJ‐H Stationary Phase

, &
Pages 513-526 | Received 14 Jul 2004, Accepted 13 Oct 2004, Published online: 07 Sep 2017

References

  • Waksmundzka‐Hajnos , M. 1998 . Chromatographic separations of aromatic carboxylic acids . J. Chromatogr. B , 717 : 93 – 118 .
  • Arai , T. 1998 . Chiral separation of pharmaceuticals possessing a carboxy moiety . J. Chromatogr. B , 717 : 295 – 311 .
  • Snyder , L. R. , Kirkland , J. J. and Glajch , J. L. 1997 . Practical HPLC Method Development , 2nd Ed. 547 New York : John Wiley & Sons .
  • Boisvert , J. , Caille , G. , McGilveray , I. J. and Qureshi , S. A. 1997 . Qua.gification of ketoprofen enantiomers in human plasma based on solid‐phase extraction and enantioselective column chromatography . J. Chromatogr. B , 690 : 189 – 193 .
  • Hoke , S. H. II , Pinkston , J. D. , Bailey , R. E. , Tanguay , S. L. and Eichhold , T. H. 2000 . Comparison of packed column supercritical fluid chromatography‐tandem mass spectrometry with liquid chromatography‐tandem mass spectrometry for bioanalytical determination of (R)‐ and (S)‐ketoprofen in human plasma following automated 96‐well solid phase extraction . Anal. Chem. , 72 : 4235 – 4241 .
  • Oliveros , L. , Senso , A. and Minguillon , C. 1997 . Benzoates of cellulose bonded on silica gel: chiral discrimination ability as high‐performance liquid chromatographic chiral stationary phases . Chirality , 9 : 145 – 149 .
  • Patel , B. K. , Valentova , J. and Hutt , A. J. 2002 . Chromatographic separation and enantiomeric resolution of flurbiprofen and its major metabolites . Chromatographia , 55 : 135 – 142 .
  • Aboul‐Enein , H. Y. , Overbeke , A. V. , Weken , G. V. , Baeyens , W. , Oda , H. , Deprez , P. and Kruif , A. D. 1998 . HPLC on Chiralcel OJ‐R for enantiomer separation and analysis of ketoprofen, from horse plasma, as the 9‐aminophenanthrene derivative . J. Pharm. Pharmacol. , 50 : 291 – 296 .
  • Zou , H. , Wang , H. and Zhang , Y. 1998 . Stereoselective binding of warfarin and ketoprofen to human serum albumin determined by microdialysis combined with HPLC . J. Liq. Chromgr. Relat. Technol. , 21 : 2663 – 2674 .
  • Zhivkova , Z. D. and Russeva , V. N. 1998 . Stereoselective binding of ketoprofen enantiomers to human serum albumin studied by high‐performance liquid chromatography . J. Chromatogr. B , 714 : 277 – 283 .
  • Baeyens , W. R.G. , Weken , G. V. , Haustraete , J. , Aboul‐Enein , H. Y. , Corveleyn , S. , Lemon , J. P. , Garcia‐Campana , A. M. and Deprez , P. 2000 . Application of the restricted‐access precolumn packing material alkyl‐diol silica in a column‐switching system for the determination of ketoprofen enantiomers in horse plasma . J. Chromatogr. A , 871 : 152 – 161 .
  • Mano , N. , Oda , Y. , Ishihama , Y. , Katayama , H. and Asakawa , N. 1998 . Investigation of interactions between drug enantiomers and flavoprotein as a chiral selector by affinity capillary electrophoresis . J. Liq. Chromatogr. Relat. Technol. , 21 : 1311 – 1332 .
  • Haginaka , J. , Kagawa , C. and Matsunaga , H. 1999 . Separation of enantiomers on a chiral stationary phase based on ovoglycoprotein VII. Comparison of chiral recognition ability of ovoglycoprotein from chicken and Japanese quail egg whites . J. Chromatogr. A , 858 : 155 – 165 .
  • Haginaka , J. 2001 . Protein‐based chiral stationary phases for high‐performance liquid chromatography enantioseparation . J. Chromatogr. A , 906 : 253 – 273 .
  • Okamoto , Y. , Kawashima , M. and Hatada , K. 1986 . Optical resolution of amino acid derivatives by high‐performance liquid chromatography on tris(phenylcarbamate)s of cellulose . J. Chromatogr. , 363 : 173
  • Okamoto , Y. , Kaida , Y. , Aburatani , R. and Hatada , K. 1989 . Chromatographic resolution XI. Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silics gel . J. Chromatogr. , 477 : 367
  • Wainer , I. W. and Alembik , M. C. 1986 . Resolution of enantiomeric amides on a cellulose‐based chiral stationary phase. Steric and electronic effects . J. Chromatogr. , 358 : 85 – 93 .
  • Wainer , I. W. , Alembik , M. C. and Smith , E. 1987 . Resolution of enantiomeric amides on a cellulose tribenzoate chiral stationary phase . J. Chromatogr. , 388 : 65 – 74 .
  • Roussel , C. , Popescu , C. and Shibata , T. 1996 . Factorial design approach to studying the high‐performance liquid chromatographic chiral separation of N‐arylthiazolin‐2‐(thi)one atropisomers on Chiralcel OJ . J. Chromatogr. A , 722 : 177 – 188 .
  • Roussel , C. and Suteu , C. 1997 . Investigation into the chiral recognition mechanism of N‐arylthiazolin‐2(thi)one atropisomers on Chilralcel OJ by factorial design and lipophilicity approaches . J. Chromatogr. A , 761 : 129 – 138 .
  • Kusters , E. and Kis , Z. L. 1997 . Enantiomeric separation of chiral theophylline derivatives by liquid chromatography on cellulose‐based sorbents . J. Chromatogr. A , 760 : 278 – 284 .
  • Ding , H. , Grinberg , N. , Thompson , R. and Ellison , D. 2000 . Enantiorecognition mechanisms for derivatized cellulose under reversed phase conditions . J. Liq. Chromgr. Relat. Technol. , 23 : 2641 – 2651 .
  • Tang , L. , Xiang , D. and Blackwell , J. A. 2000 . A comparative study of factors affecting chiral separations under reversed‐phase conditions using cellulose and pirkle‐type chiral selectors . Enantiomer , 5 : 345 – 355 .
  • Roussel , C. , Suteu , C. , Shaimi , L. and Soufiaoui , M. 1998 . Structure acid substituent effect on chiral separation of some 4a‐methyl‐2,3,4,4a‐tetrahydro‐1H‐fluorene derivatives and 4a‐methyl‐1,2,3,4,4a,9a‐ hexahydro‐fluore‐9‐one derivatives on CTA‐I and Chiralcel OJ chiral stationary phases . Chiralty , 10 : 522 – 527 .
  • O'Brien , T. , Crocker , L. , Thomson , R. , Thomson , K. , Toma , P. H. , Conlon , D. A. , Feibush , B. , Moeder , C. , Bicker , G. and Grinberg , N. 1997 . Mechanistic aspects of chiral discrimination on modified cellulose . Anal. Chem. , 69 : 1999 – 2007 .
  • Kang , G. W. , Ko , J. H. and Cheong , W. J. 2004 . Thermodynamic study of enantioseparation of arylpropionic acids with the Chirex 3001 stationary phase . J. Liq. Chromgr. Relat. Technol. , 27 : 595 – 610 .
  • Lee , C. S. and Cheong , W. J. 1999 . The non‐dispersive functional group‐solvent interaction monitored by HPLC . J. Liq. Chromgr. Relat. Technol. , 22 : 253 – 265 .
  • Lee , C. S. and Cheong , W. J. 1999 . Thermodynamic properties for the solute transfer from the moble to the stationary phase in reversed phase liquid chromatography obtained by squalane‐impregnated C18 bonded phase . J. Chromatogr. A , 848 : 9 – 20 .
  • Cheong , W. J. , Kim , C. Y. and Koo , Y. M. 2000 . Thermodynamic properties of the solute transfer from the aqueous acetonitrile mobile phase to the stationary phase monitored by HPLC . Bull. Korean Chem. Soc. , 21 : 105 – 109 .
  • Cheong , W. J. and Kim , C. Y. 2000 . The positional effect of solute functional group in hydroxyl group‐solvent and carbonyl group‐solvent specific interactions in acetonitrile/water mixed solvents monitored by HPLC . Bull. Korean Chem. Soc. , 21 : 351 – 352 .
  • Cheong , W. J. and Keum , Y. I. 2001 . Positional effect of solute functional group among positional isomers in hydroxyl group‐solvent and carbonyl group‐solvent specific interactions in methanol–water mixed solvents monitored by high performance liquid chromatography . J. Chromatogr. A , 910 : 195 – 206 .
  • Cheong , W. J. , Keum , Y. I. and Ko , J. H. 2002 . The hydroxyl group‐solvent and carbonyl group‐solvent specific interactions for some selected solutes including positional isomers in acetonitrile/water mixed solvents monitored by HPLC . Bull. Korean Chem. Soc. , 23 : 65 – 70 .
  • Okamoto , Y. , Aburatani , R. , Kaida , Y. and Harata , K. 1988 . Direct optical resolution of carboxylic acids by chiral HPLC on tris(3,5‐dimethylphenylcarbamate)s of cellulose and amylose . Chem. Lett. , : 1125 – 1128 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.