HPLC Enantiomeric Resolution of Phenyl Isothiocyanated Amino Acids on Teicoplanin‐Bonded Phase Using an Acetonitrile‐Based Mobile Phase: A Structural Consideration

References

• Shinbo , T. , Yamaguchi , T. , Nishimura , K. and Suguira , M. 1987 . Chromatographic Separation of Racemic Amino Acids by Use of Chiral Crown Ether‐Coated Reversed‐Phase Packings . J. Chromatogr. , 405 : 145 – 153 .
   PubMed Web of Science ®Google Scholar
• Hilton , M. and Armstrong , D. W. 1991 . J. Liq. Chromatogr. , 14 : 9 – 28 .
   Web of Science ®Google Scholar
• Hilton , M. and Armstrong , D. W. 1991 . J. Liq. Chromatogr. , 14 : 3673 – 3683 .
   Web of Science ®Google Scholar
• Gibitz , G. , Juffman , E. and Jelleng , W. 1982 . Chromatographia , 16 : 103 – 106 .
   Web of Science ®Google Scholar
• Davankov , V. A. and Semechkin , A. V. 1977 . J. Chromatogr. , 141 : 313 – 353 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Yang , X. , Han , S. M. and Menges , R. A. 1987 . Direct Liquid Chromatographic Separation of Racemates with an Alpha‐Cyclodextrin Bonded Phase . Anal. Chem. , 59 : 2594 – 2596 .
   PubMed Web of Science ®Google Scholar
• Fujimura , K. , Suzuki , S. , Hayashi , K. and Masuda , S. 1990 . Retention Behavior and Chiral Recognition Mechanism of Several Cyclodextrin‐Bonded Stationary Phases for Dansyl Amino Acids . Anal. Chem. , 62 : 2198 – 2205 .
   Web of Science ®Google Scholar
• Stalcup , A. M. , Jin , H. L. , Armstrong , D. W. , Mazur , P. , Derguini , F. and Nakanishi , K. 1990 . Separation of Carotenes on Cyclodextrin‐Bonded Phases . J. Chromatogr. , 499 : 627 – 635 .
   PubMed Web of Science ®Google Scholar
• Boehm , R. E. , Martire , D. E. and Armstrong , D. W. 1988 . Theoretical Considerations Concerning the Separation of Enantiomeric Solutes by Liquid Chromatography . Anal. Chem. , 60 : 522 – 528 .
   PubMed Web of Science ®Google Scholar
• Pirkle , W. H. and Pochapsky , T. C. 1986 . A New, Easily Accessible Reciprocal Chiral Stationary Phase for the Chromatographic Separation of Enantiomers . J. Am. Chem. Soc. , 108 : 352 – 354 .
   Web of Science ®Google Scholar
• Shinbo , T. , Yamaguchi , K. , Nishimura , K. and Suguira , M. 1987 . Chromatographic separation of racemic amino acids by use of chiral crown ether‐coated reversed‐phase packings . 405 : 145 – 153 .
   Google Scholar
• Chang , C. A. and Wu , Q. 1986 . Comparison of Liquid Chromatographic Separations of Geometrical Isomers of Substituted Phenols with β‐ and γ‐Cyclodextrin Bonded‐Phase Columns . Analytica Chimica Acta , 189 : 293 – 299 .
   Web of Science ®Google Scholar
• Chang , C. A. , Wu , Q. and Armstrong , D. W. 1986 . Reversed‐Phase High‐Performance Liquid Chromatographic Separation of Substituted Phenolic Compounds with a β‐Cyclodextrin Bonded Phase Column . J. Chromatogr. , 354 : 454 – 458 .
   PubMed Web of Science ®Google Scholar
• Li , W. , Chang , C. D. and Pitha , J. 1990 . Polar‐Liquid, Derivatized Cyclodextrin Stationary Phases for the Capillary Gas Chromatography Separation of Enantiomers . Anal. Chem. , 62 : 914 – 923 .
   PubMed Web of Science ®Google Scholar
• Armstrong , D. W. , Chang , C. D. and Lee , S. H. 1991 . (R)‐ and (S)‐Naphthylethylcarbamate‐Substituted β‐Cyclodextrin Bonded Stationary Phases for the Reversed‐Phase Liquid Chromatographic Separation of Enantiomers . J. Chromatogr. , 539 : 83 – 90 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Chen , S. , Chang , S. and Chang , C. 1992 . A New Approach for the Direct Resolution of Racemic Beta Adrenergic Blocking Agents by HPLC . J. Liq. Chromatogr. , 15 : 545 – 556 .
   Web of Science ®Google Scholar
• Chang , S. C. , Reid , G. L. , Chen , S. , Chang , C. D. and Armstrong , D. W. 1993 . Evaluation of a New Polar‐Organic HPLC Mobile Phase for Cyclodextrin Bonded Chiral Stationary Phase . Trends in Analytical Chemistry , 12 : 144 – 153 .
   Web of Science ®Google Scholar
• Chen , S. 1997 . High Performance Liquid Chromatographic Resolution of Dansyl Enantiomers . Chin. Pharm. J. , 49 : 51 – 60 .
   Google Scholar
• Zukowski , J. , Pawlowska , M. and Armstrong , D. W. 1992 . Efficient Enantioselective Separation and Determination of Trace Impurities in Secondary Amino Acids (i.e., Imino Acids) . J. Chromatogr. , 623 : 33 – 41 .
   PubMed Web of Science ®Google Scholar
• Zukowski , J. , Pawlowska , M. , Nagatkina , M. and Armstrong , D. W. 1988 . High‐Performance Liquid Chromatographic Enantioseparation of Glycyl Di‐ and Tripeptides on Native Cyclodextrin Bonded Phases : Mechanistic Considerations . J. Chromatogr. , 629 : 169 – 179 .
   Google Scholar
• Pawlowska , M. , Chen , S. and Armstrong , D. W. 1993 . Enantiomeric Separation of Fluorescent, 6‐Aminoquinolyl‐N‐hydroxysuccinimidyl Carbamate (AQC), Tagged Amino Acids . J. Chromatogr. , 641 : 257 – 265 .
   PubMed Web of Science ®Google Scholar
• Chen , S. , Pawlowska , M. and Armstrong , D. W. 1994 . HPLC Enantioseparation of Di‐ and Tripeptides on Cyclodextrin Bonded Stationary Phases after Derivatization with 6‐Aminoquinolyl‐N‐hydroxysuccinimidyl Carbamate (AQC) . J. Liq. Chromatogr. , 17 : 485 – 497 .
   Google Scholar
• Oi , N. and Kitahara , H. J. 1986 . Enantiomer Separation by HPLC with Urea Derivatized of L‐Valine as Novel Chiral Stationary Phases . J. Liq. Chromatogr. , 9 : 511 – 517 .
   Web of Science ®Google Scholar
• Pirkle , W. H. and Burke , J. A. 1991 . III Chiral Stationary Phase Designed for β‐Blockers . J. Chromatogr. , 557 : 173 – 185 .
   PubMed Web of Science ®Google Scholar
• Davankov , D. , Bochkov , A. , Kurganov , A. , Roumeliotis , P. and Unger , K. 1980 . Chromatographia , 13 : 677
   Web of Science ®Google Scholar
• Miwa , T. , Kuroda , H. , Sakashita , S. , Asakawa , N. and Miyake , Y. 1990 . Characteristics of Ovomucoid‐Conjugated Columns in the Direct Liquid Chromatographic Resolution of Racemic Compounds . J. Chromatogr. , 511 : 89 – 95 .
   Web of Science ®Google Scholar
• Jadaud , P. and Wainer , I. W. 1989 . Stereochemical Recognition of Enantiomeric and Diastereomeric Dipeptides by High‐Performance Liquid Chromatography on a Chiral Stationary Phase Based upon Immobilized α‐Chymotrypsin . J. Chromatogr. , 476 : 165 – 174 .
   PubMed Web of Science ®Google Scholar
• Armstrong , D. W. , Demond , W. and Czech , B. P. 1985 . Separation of Metallocene Enantiomers by Liquid Chromatography: Chiral Recognition Via Cyclodextrin Bonded Phases . Anal. Chem. , 57 : 481 – 484 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Stalcup , A. M. , Hilton , M. L. , Duncan , J. D. , Faulkner , J. and Chang , S. C. 1990 . Derivatized Cyclodextrins for Normal‐Phase Liquid Chromatographic Separation of Enantiomers . Anal. Chem. , 62 : 1610 – 1615 .
   Web of Science ®Google Scholar
• Okamoto , Y. , Hatada , K. and Aburazani , R. 1988 . Chromatographic Resolution: XXI. Direct Optical Resolution of Abscisic Acid by High‐Performance Liquid Chromatography on Cellulose Tris(3,5‐dimethylphenylcarbamate) . J. Chromatogr. , 448 : 448 – 453 .
   Web of Science ®Google Scholar
• Linder , K. R. and Mannschrek , A. 1980 . Separation of Enantiomers by High‐Performance Liquid Chromatography on Triacetylcellulose . J. Chromatogr. , 193 : 308 – 310 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Tang , Y. , Chen , S. , Zhou , Y. , Bagwill , C. and Chen , J. R. 1994 . Macrocyclic Antibiotics as a New Class of Chiral Selectors for Liquid Chromatography . Anal. Chem. , 66 : 1473 – 1484 .
   Web of Science ®Google Scholar
• Chen , S. , Liu , Y. , Armstrong , D. W. , Borrell , J. I. , Martinez‐Teipel , B. and Matallana , J. 1995 . Enantioresolution of Substituted 2‐Methoxy‐6‐oxo‐1,4,5,6‐tetrahydro‐pyridine‐3‐carbonitriles on Macrocyclic Antibiotic and Cyclodextrin Stationary Phases . J. Liq. Chromatogr. , 18 ( 8 ) : 1495 – 1507 .
   Web of Science ®Google Scholar
• Rundlett , K. L. , Gasper , M. P. , Zhou , E. Y. and Armstrong , D. W. 1996 . Capillary Electrophoretic Enantiomeric Separations Using the Glycopeptide Antibiotic, Teicoplanin . Chirality , 8 : 88 – 107 .
   Web of Science ®Google Scholar
• Ekborg‐Ott , K. H. , Liu , Y. and Armstrong , D. W. 1998 . Highly Enantioselective HPLC Separations Using the Covalently Bonded Macrocyclic Antibiotic, Ristocetin A, Chiral Stationary Phase . Chirality , 10 : 434 – 483 .
   PubMed Web of Science ®Google Scholar
• Berthod , A. , Liu , Y. , Bagwill , C. and Armstrong , D. W. 1996 . Facile Liquid Chromatographic Enantioresolution of Native Amino Acids and Peptides Using a Teicoplanin Chiral Stationary Phase . J. Chromatogr. A , 731 : 123 – 137 .
   PubMed Web of Science ®Google Scholar
• Armstrong , D. W. , Rundlett , K. and Reid , G. R. 1994 . Use of a Macrocyclic Antibiotic, Rifamycin B, and Indirect Detection for the Resolution of Racemic Amino Alcohols by CE . Anal. Chem. , 66 : 1690 – 1695 .
   PubMed Web of Science ®Google Scholar
• Ward , T. J. , Dann , C. and Blaylock , A. 1995 . Enantiomeric Resolution Using the Macrocyclic Antibiotics Rifamycin B and Rifamycin SV as Chiral Selectors for Capillary Electrophoresis . J. Chromatogr. A , 715 : 337 – 344 .
   PubMed Web of Science ®Google Scholar
• Chen , S. 2003 . The HPLC Stereoselective Resolution of N‐2, 4‐Dinitrophenylated (DNP) Amine‐Containing Enantiomers on Teicoplanin Bonded Phase Using the Methanol‐Based Mobile Phase . Chromatographia , (accepted)
   Web of Science ®Google Scholar
• Ekborg‐Ott , K. H. , Kullman , J. P. , Wang , X. , Gahm , K. , He , L. and Armstrong , D. W. 1998 . Evaluation of the Macrocyclic Antibiotic Avoparcin as a New Chiral Selector for HPLC . Chirality , 10 : 627 – 660 .
   PubMed Web of Science ®Google Scholar
• Armstrong , D. W. and Zhou , Y. 1994 . J. Liq. Chromatogr. , 17 : 1695
   Web of Science ®Google Scholar
• Armstrong , D. W. , Gasper , M. P. and Rundlett , K. L. 1995 . Highly Enantioselective Capillary Electrophoretic Separations with Dilute Solutions of the Macrocyclic Antibiotic Ristocetin A . J. Chromatogr. , 689 : 285 – 304 .
   PubMed Web of Science ®Google Scholar
• Armstrong , D. W. , Zhou , E. Y. , Chen , S. , Le , K. and Tang , Y. 1994 . Foam Flotation Enrichment of Enantiomers . Anal. Chem. , 66 : 4278 – 4282 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Tang , Y. , Ward , T. and Nichols , M. 1993 . Derivatized Cyclodextrins Immobilized on Fused‐Silica Capillaries for Enantiomeric Separations via Capillary Electrophoresis, Gas Chromatography, or Supercritical Fluid Chromatography . Anal. Chem. , 65 : 1114 – 1117 .
   Web of Science ®Google Scholar
• Edman , P. 1950 . The Amino Acid Sequence of Neurotoxin I of Androctonus Australis Hector . Acta Chem. Scand. , 4 : 283 – 295 .
   Google Scholar
• Edman , P. and Begg , G. 1967 . A Protein Sequenator . Eur. J. Biochem. , 1 : 80 – 91 .
   PubMedGoogle Scholar
• Stark , R. G. 1971 . “ In Biochem ” . In Aspects of Reactions on Solid Supports 171 – 188 . New York : Academic Press .
   Google Scholar
• Ebert , R. F. 1986 . Amino Acid Analysis by HPLC: Optimized Condition for Chromatography of Phenylthiocarbamyl Derivatives . Anal. Biochem. , 154 : 431 – 435 .
   PubMed Web of Science ®Google Scholar
• Heinrikson , R. L. and Meredith , S. C. 1984 . Amino Acid Analysis by Reversed‐Phase High‐Performance Liquid Chromatography: Precolumn Derivatization with Phenylisothiocyanate . Anal. Biochem. , 136 : 65 – 74 .
   PubMed Web of Science ®Google Scholar
• Chen , S. 1996 . The Enhanced Chiral Resolution of Enantiomers on Cyclodextrin Bonded Stationary Phases by Modifying the Additives in Nonaqueous Acetonitrile‐Based Mobile Phases . J. Chin. Chem. Soc. , 43 : 503 – 506 .
   Web of Science ®Google Scholar
• Pirkle , W. H. , Pochapsky , T. C. , Mahler , G. S. and Field , R. E. 1985 . Chromatographic Separation of the Enantiomers of 2‐Carboalkoxyindolines and N‐Aryl‐α‐Amino Esters on Chiral Stationary Phases Derived From N‐(3,5‐Dinitrobenzoyl)—Amino Acids . J. Chromatogr. , 348 : 89 – 96 . 53
   Web of Science ®Google Scholar