Separation of cis-β-lactam enantiomers by capillary electrophoresis using cyclodextrin derivatives

Journal of Pharmaceutical and Biomedical Analysis

Volumn 53, Issue 3, 2010, Pages 382-388

  Németh, Krisztina ^a   Varga, Erzsébet ^b   Iványi, Róbert ^b   Szemán, Julianna ^b   Visy, Júlia ^a   Jicsinszky, László ^b   Szente, Lajos ^b   Forró, Eniko ^c   Fülöp, Ferenc ^c   Péter, Antal ^d   Simonyi, Miklós ^a  

^a CHEMICAL RESEARCH CENTER   (Hungary)

^b CycloLab Cyclodextrin Research & Development Laboratory Ltd   (Hungary)

^c UNIVERSITY OF SZEGED   (Hungary)

^d UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Apparent complex stability constant; Capillary electrophoresis; Chiral separation of lactams; Dual cyclodextrin system; Reversed order of enantiomer migration

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; BETA CYCLODEXTRIN; BETA LACTAM; CARBOXYMETHYL ALPHA CYCLODEXTRIN; CARBOXYMETHYL BETA CYCLODEXTRIN; CARBOXYMETHYL GAMMA CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; ELECTROLYTE; PERMETHYLATED BETA CYCLODEXTRIN; RANDOMLY METHYLATED BETA CYCLODEXTRIN; SULFOBUTY BETA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; ENANTIOMER; PH; PRIORITY JOURNAL; STEREOISOMERISM;

BETA-CYCLODEXTRINS; BETA-LACTAMS; DRUG STABILITY; ELECTROPHORESIS, CAPILLARY; STEREOISOMERISM;

EID: 77954864316     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2010.04.026     Document Type: Article

References (30)

1. Mantagne A., Lamotte-Brasseur J., Frere J.M. Catalytic properties of class A β-lactamases: efficiency and diversity. Biochem. J. 1998, 330:581-598.
2. Lamotte J., Dive G., Ghuysen J.M. Conformational analysis of β- and γ-lactam antibiotics. Eur. J. Med. Chem. 1991, 26:43-50.
3. Palomo C., Aizpurua J.M., Ganboa I., Oiaribe M. β-Lactams as versatile intermediates in α and β-amino acid synthesis. Synlett 2001, 12:1813-1826.
4. Palomo C., Ganboa I., Oiaribe M., Sciano G.T., Miranda J.L. A β-lactam route to short peptide segments to angiotensin-converting enzyme (ACE) inhibitors. ARKIVOC 2002, 5:8-16.
5. Juaristi E. Enantioselective Synthesis of β-Amino Acids 1997, Wiley-VCH, New York.
6. Wasserman H.H., Matsuyama H., Robinson R.P. β-Lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids. Tetrahedron 2002, 58:7177-7190.
7. Alcaine B., Almendros P., Alonso J.M., Aly M.F., Padro C., Saez E., Torres M.R. Efficient entry to highly functionalized β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction of 2-azetidinone-tethered nitrones, synthetic application. J. Org. Chem. 2002, 67:7004-7013.
8. Achilles K., Schirmeister T., Otto H.H. β-Lactam derivatives as enzyme inhibitors: 1-peptidyl derivatives of 4-phenylazetidin-2-one as inhibitors of elastase and papain. Arch. Pharm. Pharm. Med. Chem. 2000, 333:243-253.
9. Huang K., Armstrong D.W., Forró E., Fülöp F., Péter A. Separation of enantiomers and control of elution order of β-lactams by GC using cyclodextrin-based chiral stationary phases. Chromatographia 2009, 69:331-337.
10. Berkecz R., Török R., Ilisz I., Forró E., Fülöp F., Armstrong D.W., Péter A. LC enantioseparation of β-lactam and β-amino acid stereoisomers and a comparison of macrocyclic glycopeptide- and β-cyclodextrin-based columns. Chromatographia 2006, 63:S37-S43.
11. Sun P., Wang C., Armstrong D.W., Péter A., Forró E. Separation of enantiomers of β-lactams by HPLC using cyclodextrin-based chiral stationary phases. J. Liq. Chromatogr. Relat. Technol. 2006, 29:1847-1860.
12. Péter A., Árki A., Forró E., Fülöp F., Armstrong D.W. Direct high-performance liquid chromatographic enantioseparation of β-lactam stereoisomers. Chirality 2005, 17:193-200.
13. Pataj Z., Ilisz I., Berkecz R., Forró E., Fülöp F., Péter A. Comparison of separation performances of amylase- and cellulose-based stationary phases in the high-performance liquid chromatographic enantioseparation of stereoisomers of β-lactams. Chirality 2010, 22:120-128.
14. Fillet M., Hubert P., Crommen J. Enantiomeric separations of drugs using mixtures of charged and neutral cyclodextrins. J. Chromatogr. A 2000, 875:123-134.
15. Izumoto S.-I., Nishi H. Enantiomer separation of drugs by capillary electrophoresis using mixtures of β-cyclodextrin sulphate and neutral cyclodextrins. Electrophoresis 1999, 20:189-197.
16. Fillet M., Chankvetadze B., Crommen J., Blaschke G. Designed combination of chiral selectors for adjustment of enantioseparation selectivity in capillary electrophoresis. Electrophoresis 1999, 20:2691-2697.
17. Dubsky P., Svobodova J., Gas B. Model of CE enantioseparation systems with a mixture of chiral selectors. Part I: Theory of migration and interconversion. J. Chromatogr. B 2008, 875:30-34.
18. Sepeniak M.J., Copper C.L., Whitaker K.W., Anigbogu V.C. Evaluation of dual-cyclodextrin phase variant of capillary electrokinetic chromatography for separation of nonionizable solutes. Anal. Chem. 1995, 67:2037-2041.
19. Lurie I.S., Klein R.F.X., Dal Cason T.A., LeBelle M.J., Brenneisen R., Weinberger R.E. Chiral resolution of cationic drugs of forensic interest by capillary electrophoresis with mixtures of neutral and anionic cyclodextrins. Anal. Chem. 1994, 66:4019-4026.
20. Lurie I.S. Separation selectivity in chiral and achiral capillary electrophoresis with mixed cyclodextrins. J. Chromatogr. A 1997, 792:297-307.
21. Abustoffa A.M., Fillet M., Hubert P., Crommen J. Prediction of selectivity for enantiomeric separations of uncharged compounds by capillary electrophoresis involving dual cyclodextrin systems. J. Chromatogr. A 2002, 948:321-329.
22. Fillet M., Fotsing L., Crommen J. Enantioseparation of uncharged compounds by capillary electrophoresis using mixtures of anionic and neutral β-cyclodextrin derivatives. J. Chromatogr. A 1998, 817:113-119.
23. Surapanemi S., Ruterbories K., Lindstrom T. Chiral separation in capillary electrophoresis using dual neutral cyclodextrins: theoretical models. J. Chromatogr. A 1997, 761:249-257.
24. Terabe S., Ozaki H., Otsuka K., Ando T. Electrokinetic chromatography with 2-O-carboxymethyl-β-cyclodextrin as a moving "stationary" phase. J. Chromatogr. 1985, 332:211-217.
25. Jiang C., Armstrong D.W., Péter A., Fülöp F. Enantiomeric separation of a series of β-lactams using capillary zone electrophoresis. J. Liq. Chromatogr. Relat. Technol. 2007, 30:1709-1721.
26. Fülöp F. The chemistry of 2-aminocycloalkanecarboxylic acids. Chem. Rev. 2001, 101:2181-2204.
27. Forró E., Árva J., Fülöp F. Preparation of (1R,8S)-9-azabicyclo[6.2.0]-dec-4-en-10 one: potential strating compounds for synthesis of anatoxin. Tetrahedron-Asymmetry 2001, 12:643-649.
28. Berkecz R., Ilisz I., Forró E., Fülöp F., Armstrong D.W., Péter A. LC enantioseparation of aryl-substituted β-lactams using variable-temperature conditions. Chromatographia 2006, 63:S29-S35.
29. Fanali S. Controlling enantioselectivity in chiral capillary electrophoresis with inclusion-complexation. J. Chromatogr. A 1997, 792:227-267.
30. Bellini M.S., Deyl Z., Manetto G., Kohlicková M. Determination of apparent binding constants of drugs by capillary electrophoresis using β-cyclodextrin as ligand and three different linear plotting methods. J. Chromatogr. A 2001, 924:483-491.