Liquid Chromatographic Enantiomer Separation of N‐Phthaloyl Protected α‐Amino Acids on Coated and Immobilized Chiral Stationary Phases Derived from Polysaccharide Derivatives

References

• Sheldon , R. A. 1993 . Chirotechnology: Industrial Synthesis of Optically Active Compounds New York : Marcel Dekker .
   Google Scholar
• Bodansky , M. and Bodansky , A. 1984 . The Practice of Peptide Synthesis New York : Springer .
   Google Scholar
• Subramanian , G. , ed. 1994 . A Practical Approach to Chiral Separations by Liquid Chromatography New York : VCH .
   Google Scholar
• Greene , T. W. and Wuts , P. G.M. 1999 . Protective Groups in Organic Synthesis , 3rd Ed. New York : John Wiley & Sons. Inc. .
   Google Scholar
• Birch , D. , Hill , R. R. , Jeffs , G. E. and North , M. 1999 . Stereochemical preference for heterochiral coupling controls selectivity in competitive peptide synthesis . Chem. Commun. , : 941 – 942 .
   Google Scholar
• Lei , A. , Wu , S. , He , M. and Zhang , X. 2004 . Highly enantioselective asymmetric hydrogenation of α‐phthalimide ketone: an efficient entry to enantiomerically pure amino alcohols . J. Am. Chem. Soc. , 126 : 1626 – 1627 .
   PubMed Web of Science ®Google Scholar
• Müller , R. , Goesmann , H. and Waldmann , H. 1999 . N,N‐Phthaloylamino acids as chiral auxiliaries in asymmetric Mannich‐type reactions . Angew. Chem. Int. Ed. , 38 : 184 – 187 .
   Web of Science ®Google Scholar
• Müller , R. , Röttele , H. , Henke , H. and Waldmann , H. 2000 . Asymmetric steering of the Mannich reaction with phthaloyl amino acids . Chem. Eur. J. , 6 : 2032 – 2043 .
   PubMedGoogle Scholar
• Krasnov , V. P. , Levit , G. L. , Kodess , M. I. , Charushin , V. N. and Chupakhin , O. N. 2004 . N‐Phthaloyl‐(S)‐alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines . Tet. Asymm. , 15 : 859 – 62 .
   Google Scholar
• Skowronek , P. , Katrusiak , A. and Gawronski , J. 2002 . Phthalimide as a chromophoric tag in the circular dichroism determination of absolute configuration of α‐aminoacid amides and dipeptides. A case of a dipeptide isostructurality . Tetrahedron , 58 : 10463 – 10468 .
   Google Scholar
• Pirkle , W. H. and Lee , W. 1998 . Separation of the enantiomers of N‐benzyloxycarbonyl, 9‐fluoromethoxycarbonyl and phthaloyl protected α‐amino acids and their ester or amide derivatives . Bull. Kor. Chem. Soc. , 19 : 1277 – 1280 .
   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
• Zhang , T. , Kientzy , C. , Franco , P. , Ohnishi , A. , Kagamihara , Y. and Kurosawa , H. 2005 . Solvent versatility of immobilized 3,5‐dimethylphenylcarbamate of amylose in enantiomeric separations by HPLC . J. Chromatogr. A , 1075 : 65 – 75 .
   PubMed Web of Science ®Google Scholar
• Zhang , T. , Nguyen , D. , Franco , P. , Murakami , T. , Ohnishi , A. and Kurosawa , H. 2006 . Cellulose 3,5‐dimethylphenylcarbamate immobilized on silica: A new chiral stationary phase for the analysis of enantiomers . Anal. Chim. Acta , 557 : 221 – 228 .
   Web of Science ®Google Scholar
• Jin , J. Y. , Lee , W. , Park , J. H. and Ryoo , J. J. 2006 . Covalently bonded and coated chiral stationary phases derived from polysaccharide derivatives for Enantiomer Separation of N‐fluorenylmethoxycarbonyl α‐amino acids with fluorescence detection . J. Liq. Chromatogr. & Rel. Technol. , 29 : 1793 – 1801 .
   Web of Science ®Google Scholar
• McArthur , C. R. , Worster , P. M. and Okon , A. U. 1983 . Amino group blocking: Improved method for N‐phthaloylation using N‐(ethoxycarbonyl)phthalimide . Syn. Commun. , 13 : 311 – 318 .
   Web of Science ®Google Scholar
• Lee , W. 1999 . Separation of the enantiomers of amino acid esters as benzophenone imine derivatives using polysaccharide derived chiral stationary phases . Chromatographia , 49 : 61 – 64 .
   Google Scholar
• Application Guide for Chiral HPLC selection , 4th ed. Daicel Chemical Industries, Ltd .
   Google Scholar
• Jin , J. Y. , Lee , W. and Hyun , M. H. 2006 . Development of the antipode of the covalently‐bonded crown ether type chiral stationary phase for the advantage of the reversal of elution order . J. Liq. Chromatogr. & Rel. Technol. , 29 : 841 – 848 .
   Web of Science ®Google Scholar