Preparation of a New π-Basic Chiral Stationary Phase Based on Cefaclor and the Liquid Chromatographic Resolution of π-Acidic Analytes

REFERENCES

• Crossley , R. Chirality and the Biological Activity of Drugs ; CRC Press : Boca Raton , 1995 .
   Google Scholar
• Subramanian , G. , Ed. Chiral Separation Techniques; A Practical Approach. Third Completely Revised and Updated Edition ; Wiley-VCH : Weinheim , 2007 .
   Google Scholar
• Yashima , E. Polysaccharide-based chiral stationary phases for high-performance liquid chromatographic enantioseparation . J. Chromatogr. A 2001 , 906 , 105 – 125 .
   PubMed Web of Science ®Google Scholar
• Allenmark , S. Optical resolution by liquid chromatography on immobilized bovine serum albumin . J. Liq. Chromatogr. 1986 , 9 , 425 – 442 .
   Web of Science ®Google Scholar
• Hyun , M.H. ; Lee , J.B. ; Kim , Y.D. An improved (S)-leucine-derived π-acidic HPLC chiral stationary phase for the resolution of π-acidic racemates . J. High Resol. Chromatogr. 1998 , 21 , 69 – 71 .
   Google Scholar
• Ward , T.J. ; Farris III , A.B. Chiral separations using the macrocyclic antibiotics: A review. J. Chromatogr. A. 2001, 906, 73–89.
   PubMed Web of Science ®Google Scholar
• Hyun , M.H. ; Jin , J.S. ; Lee , W. Liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether . J. Chromatog. A. 1998 , 822 , 155 – 161 .
   Web of Science ®Google Scholar
• Hyun , M.H. ; Han , S.C. ; Lipshutz , B.H. ; Shin , Y.-J. ; Welch , C.J. New chiral crown ether stationary phase for the liquid chromatographic resolution of α-amino acid enantiomers . J. Chromatogr. A. 2001 , 910 , 359 – 365 .
   PubMed Web of Science ®Google Scholar
• Cho , Y.J. ; Choi , H.J. ; Hyun , M.H. Preparation of two new liquid chromatographic chiral stationary phases based on diastereomeric chiral crown ethers incorporating two different chiral units and their applications . J. Chromatogr. A. 2008 , 1191 , 193 – 198 .
   Google Scholar
• Pirkle , W.H. ; Welch , C.J. ; Lamm , B. Design, synthesis, and evaluation of an improved enantioselective naproxen selector . J. Org. Chem. 1992 , 57 , 3854 – 3860 .
   Web of Science ®Google Scholar
• Gasparrini , F. ; Misiti , D. ; Villani , C. High-performance liquid chromatography chiral stationary phases based on low-molecular-mass selector . J. Chromatogr. A 2001 , 906 , 35 – 50 .
   PubMed Web of Science ®Google Scholar
• Hyun , M.H. ; Boo , C.J. ; Choi , H.J. ; Kim , Y.K. ; Kang , B.S. ; Ha , H.J. ; Choi , M.K. ; Tan , G. Preparation of a new chiral stationary phase based on (2S,3S)-O,O′-Bis-(10-undecenoyl)-N,N′-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butandiol and its application for the liquid chromatographic resolution of enantiomers . Bull. Kor. Chem. Soc. 2006 , 27 , 1769 – 1774 .
   Google Scholar
• Hyun , M.H. ; Kim , S.N. ; Choi , H.J. ; Sakthivel , P. Liquid chromatographic resolution of N-(3,5-Dinitrobenzoyl)-α-amino acids on a new chiral stationary phase: The first liquid chromatographic utilization of a double-ureide pocket for the recognition of chiral carboxylate Anions . Bull. Kor. Chem. Soc. 2007 , 28 , 1980 – 1984 .
   Google Scholar
• Hyun , M.H. ; Kim , S.N. ; Choi , H.J. ; Sakthivel , P. Preparation and application of a new ion-pairing chiral stationary phase for the liquid chromatographic resolution of N-(3,5-dinitrobenzoyl)-α-amino acids . J. Liq. Chromatogr. & Rel. Technol. 2008 , 31 , 2363 – 2374 .
   Web of Science ®Google Scholar
• Cho , H.S. ; Ha , H.J. ; Choi , H.J. ; Jin , J.S. ; Hyun , M.H. Preparation and application of a new liquid chromatographic chiral stationary phase based on cefaclor . Bull. Kor. Chem. Soc. 2008 , 29 , 2135 – 2139 .
   Google Scholar
• Hyun , M.H. ; Kim , Y.D. ; Han , S.C. ; Lee , J.B. A chiral recognition mechanism proposed for resolving π-acidic racemates on a π-acidic chiral stationary phase derived from (S)-leucine . J. High. Resol. Chromatogr. 1998 , 21 , 464 – 470 .
   Google Scholar
• Mennini , T. ; Caccia , S. ; Garattini , S. Mechanism of action of anxiolytic drugs . Prog. Drug. Res. 1987 , 31 , 315 – 347 .
   PubMedGoogle Scholar
• Savadori , P. ; Bertucci , C. ; Domenici , E. ; Giannaccini , G. Chiral 1,4-benzodiazepin-2-ones: Relationship between stereochemistry and pharmacological activity . J. Pharm. Biomed. Anal. 1989 , 7 , 1735 – 1742 .
   Google Scholar
• Pirkle , W.H. ; Tsipouras , A. Direct liquid chromatographic separation of benzodiazepine enantiomers . J. Chromatogr. 1984 , 291 , 291 – 298 .
   Web of Science ®Google Scholar
• Hyun , M.H. ; Cho , Y.J. ; Kim , J.A. Liquid chromatographic resolution of racemic 1,4-benzodiazepin-2-ones on Pirkle-type chiral stationary phases based on (S)-leucine . Bull. Kor. Chem. Soc. 2005 , 26 , 823 – 825 .
   Google Scholar
• Choi , H.J. ; Kim , Y.K. ; Hyun , M.H. Liquid chromatographic resolution of racemic 1,4-benzodiazepin-2-ones on a chiral stationary phase based on N,N′-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butandiol. Bull. Kor. Chem. Soc. 2008, 29, 1850–1852.
   Google Scholar