Макроциклические модификаторы для повышения селективности электрофоретического разделения энантиомеров органических кислот
Диссертация
Научная новизна. Показана эффективность макроциклического гликопептидного антибиотика эремомицина в качестве хирального селектора в КЭ. Установлен характер влияния эремомицина на величину и направление электроосмотического потока. Получены количественные характеристики адсорбции эремомицина на поверхности кварцевого-капилляра, что позволило разработать способ динамического модифицирования… Читать ещё >
Список литературы
- Карцова, JI.A., Сидорова, А.А., Иванова, А. С. Электрофоретическое определение биогенных аминов в биологических жидкостях // Журн. аналит. химии. 2007. Т.62. С. 106 671.
- Chankvetadze, В. Separation selectivity in chiral capillary electrophoresis with charged selectors //J. Chromatogr. A. 1997. V.792. P.269−95.
- Soga, Т., Ross, G.A. Simultaneous determination of inorganic anions, organic acids, amino acids and carbohydrates by capillary electrophoresis // J. Chromatogr. A. 1999. V.837. P.231−9.
- Jorgenson, J.W., Lukacs, K.D. Zone electrophoresis in open-tubular glass capillaries // Anal. Chem. 1981. V.53. P.1298−302.
- Liu, X., Frank, H. Separation of chlorophenols by capillary zone electrophoresis. The influence of pH of the electrophoretic buffer on selectivity // J. High Resol. Chromatogr. 1998. Y.21. P.309−14.
- Fanali, F., Cartoni, C., Desiderio, C. Chiral separation of newly synthesized arylpropionic acids by capillary electrophoresis using cyclodextrins or a glycopeptide antibiotic as chiral selectors // Chromatographia. 2004. V.54. P.87−92.
- Desiderio, C., Polcaro, C.M., Padiglioni, P., Fanali, F. Enantiomeric separation of acidic herbicides by capillary electrophoresis using vancomycin as chiral selector // J. Chromatogr. A. 1997. V.871. P.503−13.
- Okada, T. Non-aqueous capillary electrophoretic separation of Bronsted acids as heteroconjugated anions // J. Chromatogr. A. 1997. V.771. P.275−84.
- Riekkola, M.-L., Wiedmer, S.K., Valko, I.E., Siren, H. Selectivity in capillary electrophoresis in the presence of micelles, chiral selectors and non-aqueous media // J. Chromatogr. A. 1997. V.792. P.13−35.
- Kang, J.-W., Yang, Y.-T., You, J.-M., Ou, Q.-Y. Fast chiral separation of amino acid derivatives and acidic drugs by co-electroosmotic flow capillary electrophoresis with vancomycin as chiral selector// J. Chromatogr. A. 1998. V.825. P.81−7.
- Ong, C.P., Ng, C.L., Chong, N.C., Lee, H., Li, S.F.Y. Retention of eleven priority phenols using micellar electrokinetic chromatography // J. Chromatogr. A. 1990. V.516. P.263−7.
- Пирогов, A.B., Степанов, K.B., Шпигун, O.A. Изменение электрофоретической подвижности фенолов при использовании) добавок ионенов в буферный электролит // Журн. аналит. химии. 2003. Т.58. С.478−84.
- Horvath, J., Dolnik, V. Polymer wall coatings for capillary electrophoresis // Electrophoresis. 2001. Y.22. P.644−55.
- Cifuentes, A., Canalejas, P., Ortega, A., Diez-Masa, J.C. Treatments of fused-silica capillaries and their influence on the electrophoretic characteristics of these columns before and after coating // J. Chromatogr. A. 1998. V.823. P.561−71.
- Towns, J.K., Bao, J., Regnier, F.E. Synthesis and evaluation of epoxy polymer coatings for the analysis of proteins by capillary zone electrophoresis // J. Chromatogr. 1992. V.599. P.227−37.
- Regnier, F., Noel, R. Glycerolpropylsilane bonded phases in the steric exclusion chromatography of biological macromolecules // Chromatogr. Sci. 1976. V.14. P.316−20.
- Shao, X., Shen, Y., O’Neill, K., Lee, M.L. Capillary electrophoresis using diol-bonded fused-silica capillaries // J. Chromatogr. A. 1999. V.830. P.415−22.
- Cobb, K.A., Dolnik, V., Novotny, M. Electrophoretic separations of proteins in capillary with hydrolitically-stable surface structure // Anal. Chem. 1990. V.62. P.2478−83.
- Nakatani, M., Skibukawa, A., Nakagawa, T. Preparation and characterization of a stable polyacrylamide sieving matrix-filled capillary for high-performance capillary electrophoresis // J. Chromatogr. A. 1994. V.661. P.315−21.
- Guo, Y., Imahori, G., Colon, L. Hydrolytically stable amino-silica glass coating material for manipulation of the electroosmotic flow in capillary electrophoresis // J. Chromatogr. A. 1996. V.744. P. 17−29.
- Hjerten, S. High-performance electrophoresis elimination of electroendosmosis and solute adsorption. // J. Chromatogr. 1985. V.347. P.191−8.
- Wang, Z., Wang, J., Hu, Z., Kang, J. Enantioseparation by CE with vancomycin as chiral selector: Improving the separation performance by dynamic coating of the capillary with poly (dimethylacrylamide) // Electrophoresis. 2007. V.28. P.938−43.
- Giibitz, G., Schmid, M.G. Chiral separation by capillary electromigration techniques // J. Chromatogr. A. 2008. V.1204. P. 140−56.
- Chankvetadze, B. Separation of enantiomers with charged chiral selectors in CE // Electrophoresis. 2009. V.30. P. S211−21.
- Ycspalec, R., Bocek, P. Chiral separations in. capillary electrophoresis // Chem. Rev. 2000. V.100. P.3715−53.
- Комарова, H.B., Каменцев, Я.С. Практическое руководство по использованию систем капиллярного электрофореза «Капель». СПб.: ООО «Веда», 2006. 212 с.
- Armstrong, D.W., Rundlett, K.L., Reid- III G.L. Use of a macrocyclic antibiotic, rifamycin B, and indirect detection for the resolution of racemic amino alcohols by CE // Anal. Chem. 1994. V.66. P.1690−5.
- Ward, T.J., Dann, III C., Blaylock, A. Enantiomeric resolution using tlir macrocyclic antibiotics rifamycin В and rifamycin SV as chiral selectors in capillary electrophoresis // J. Chromatogr. A. 1995. V.715. P.337−44.
- Armstrong, D.W., Tang, Y., Chen, S., Zhou, Y., Bagwill, C., Chen, J.-R. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography // Anal. Chem. 1994. V.66. P.1473−84.
- Nishi, H., Nakamura, K., Nakai, H., Sato, T. Enantiomer separation by capillai-y electrophoresis using DEAE-Dextran and aminoglycosidic antibiotics // Chromatographia. 1996. V.43. P.426−30.
- Chen, В., Du, Y., Wang, H. Study on enantiomeric separation of basic drugs by NACE in methanol-based medium using erythromycin lactobionate as a chiral selector // Electrophoresis. 2010. V.31. P.371−7.
- Hou, J., He, Т., Han, X., Du, X., Мао, X., Deng, H., Gao, J. Chiral Separation of Erythromycin as a New Chiral Selector on CE. // Chin. Chem. Lett. 2003. V.14. P.280−2.
- Chen, В., Du, Y., Li, P. Investigation of enantiomeric separation of basic drugs by capillary electrophoresis using clindamycin phosphate a a novel chiral selector // Electrophoresis. 2009. V.30. P.2747−54.
- Rundlett, K.L., Gasper, M.P., Zhou, E.Y., Armstrong, D.W. Capillary electrophoretic enantiomeric separations using the glycopeptide antibiotic, teicoplanin. // Chirality. 1996. V.8. P.88−107.
- Gerhard, U., Mackay, J.P., Maplestone, R.A., Williams, D.H. The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics // J. Am, Chem. Soc. 1993. V. l 15. P.232−7.
- Slama, I., Dufresne, C., Jourdan, E., Fahrat, F., Villet, A., Ravel, A., Grosset, C., Peyrin, E. Vancomycin Dimerization and Chiral Recognition Studied by High-Performance Liquid' Chromatography // Anal. Chem. 2002. V.74. P.5205−11.
- Slama, I., Jourdan, E., Grosset, C., Ravel, A., Villetm A., Peyrinm E. Role of the vancomycin-ristocetin heterodimerization on the enantioselectivity of D, L-tryptophan and D, L-dansyl tryptophan // J. Chromatogr. B. 2003. V.795. P. 115−21.
- Armstrong, D.W., Rundlett K.L., Chen, J.-R. Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis // Chirality. 1994. V.6. P.496−504.
- Armstrong, D.W., Gasper, M.P., Rundlett, K.L. Highly enantioselective capillary electrophoretic separations with dilute solutions of the macrocyclic antibiotic ristocetin A // J. Chromatogr. A. 1995. V.689. P.285−304.
- Armstrong, D.W., Rundlett, K.L. CE resolution of neutral and anionic racemates with glycopeptide antibiotics and micelles // J. Liq. Chrom. 1995. V.18. P.3659−74.
- Rundlett, K.L., Armstrong, D.W. Effect of micelles and mixed micells on efficiency and selectivity of antibiotic-based capillary electrophoretic enantioseparations // Anal. Chem. 1995. V.67. P.2088−95.
- Vespalec, R., Corstjens, H., Billiet, H.A.H., Frank, J., Luyben, K.C.A.M. Enantiomeric separation of sulfur- and selenium-containing amino acids by capillary electrophoresis using vancomycin as a chiral selector // Anal. Chem. 1995. Y.67. P.3223−8.
- Arai, T., Nimura, N., Kinoshita, T. Investigation of enantioselective separation of quinolonecarboxilic acid by capillary zone electrophoresis using vancomycin as chiral selector // J. Chromatogr. A. 1996. V.739. P.303−11.
- Fanali, F., Desiderio, C. Use of vancomycin as chiral selector in capillary electrophoresis. Optimization and quantitation of loxiglumide enantiomers in pharmaceuticals // J. High Resol. Chromatogr. 1996. V.19. P.322−6.
- Strege, M.A., Huff, B.E., Risley, D.S. Evaluation of macrocyclic antibiotic A82846B as a chiral selector for capillary electrophoresis separations // LC-GC. 1996. V.14. P. 144−50.
- Vespalec, R., Billiet, H.A.H., Frank, J., Bocek, P. Vancomycin as a chiral selector in capillary electrophoresis: An appraisal of advantages and limitations // Electrophoresis. 1996. V.17. P.1214−21.
- Wan, H., Blomberg, L.G. Enantioseparation of amino acids and dipeptides using vancomycin as chiral selector in capillary electrophoresis // Electrophoresis. 1996. V.17. P. 193 844.
- Wan,* H., Blombeig, L. Enantiomeric separation by capillary electrophoresis of di- and tri-peptides derivatized with' 9-fluorenylmethyl chloroformate using vancomycin as chiral selector//J. Micro. SeP. l996. V.8. P.339−44.
- Ward, T.J., Dann, III C., Brown, A.P. Separation of enantiomers using vancomycin in a countercurrent process by supression of electrosmosis // Chirality. 1996. V.8. P.77−83.
- Fanali, S., Desiderio, C., Aturki, Z. Enantiomeric resolution study by capillary electrophoresis. Selection of the appropriate chiral selector // J. Chromatogr. A. 1997. V.772. P. 185−94.
- Sharp, V.S., Risley, D.S., McCarthy, A., Huff, B.E., Strege, M.A. Evaluation of a new macrocyclic antibiotic as a chiral selector for use in capillary electrophoresis // J. Liq. Chrom. & Rel. Technol. 1997. V.20. P.887−98.
- Ekborg-Ott, K.H., Zientara, G.A., Schneiderheinze, J.M., Gahm, K., Armstrong D.W. Avoparcin, a new macrocyclic antibiotic chiral run buffer additive for capillary electrophoresis // Electrophoresis. 1999. V.20. P.2438−57.
- Fanali, S., Aturki, Z., Desiderio, C., Righetti, P.G. Use of MDL 63 246 (Hepta-Tyr) antibiotic in capillary zone electrophoresis II. Chiral resolution of a-hydroxy acids // J. Chromatogr. A. 1999. V.838. P.223−35.
- Oswald, T.M., Ward, T.J. Enantioseparations with the macrocyclic antibiotic ristocetin A using a countercurrent process in CE // Chirality. 1999. V. l 1. P.663−8.
- Risley, D.S., Trelli-Seifert, L., McKenzie, Q.J. Enantiomeric separations of dansyl amino acids using the macrocyclic antibiotic A35512B as a chiral selector in capillary electrophoresis // Electrophoresis. 1999. V.20. P.2749−53.
- Bednar, P., Aturki, Z., Stransky, Z., Fanali, S. Chiral analysis of UV nonabsorbing compounds by capillary electrophoresis using macrocyclic antibiotics: 1. Separation of aspartic and glutamic acid enantiomers // Electrophoresis. 2001. V.22. P.2129−35.
- Fanali, F., Cartoni, C., Aturki, Z. Enantioseparation of S-carboxymethylcysteine and N-acetamidocarboxymethylcysteine by capillary electrophoresis using vancomycin // J. SeP.Sci. 2001. V.24. P.789−94.
- Ha, P., Van Schepdael, A., Roets, E., Hoogmartens, J. Investigating the potential of erythromycin and derivatives as chiral selector in capillary electrophoresis // J. Pharm. Biomed. Anal. 2004. V.34. P.861−70.
- Jiang, Z., Kang, J., Bischoff, D., Bister, Bi, Sussmuth, R.D., Schurig, V. Evaluation of balhimycin as ai chiral selector for enantioresolution by capillary electrophoresis // Electrophoresis. 2004. V.25. P.2687−92.
- Fantacuzzi, M., Bettoni, G., D’Orazio, G., Fanali, S. Enantiomeric separation of some demethylated analogues of clofibric acid by capillary zone electrophoresis and', nano-liquid chromatography // Electrophoresis. 2006. V.27. P. 1227−36.
- Ward, T.J., Oswald, T.M. Enantioselectivity in capillary electrophoresis using the macrocyclic antibiotics // J. Chromatogr. A. 1997. V.792. P.309−25.
- Desiderio, C., Fanali, S. Chiral analysis by capillary electrophoresis using antibiotics as chiral selector//J. Chromatogr. A. 1998. V.807. P.37−56.
- Fanali, S., Aturki, Z., Desiderio, C., Bossi, A., Righetti, P.G. Use of a Hepta-tyr glycopeptide antibiotic as chid selector in capillary electrophoresis // Electrophoresis. 1998. V.19. P. 1742−51.
- LeTourneau, D.L., Allen, N.E. Use of capillary electrophoresis to measure dimerization of glycopeptide antibiotics // Anal. Biochem. 1996. V.246. P.62−6.
- Gasper, M.P., Berthod, A., Nair, U.B., Armstrong, D.W. Comparison and modeling study of vancomycin, ristocetin A, and teicoplanin for CE enantioseparations // Anal. Chem. 1996. V.68. P.2501−14.
- Fanali, S., Crucianelli, M., De Angelis, F., Presutti, C. Enantioseparation of amino acid derivatives by capillary zone electrophoresis using vancomycin as chiral selector // Electrophoresis. 2002. V.23. P.3035−40.
- Fanali, S., Desiderio, C., Schulte, G., Heitmeier, S., Strickmann, D., Chankvetadze, B., Blaschke G. Chiral capillary electrophoresis-electrospray mass spectrometry coupling using vancomycin as chiral selector // J. Chromatogr. A. 1998. V.800. P.69−76.
- Du, Y., Chen, B. Evaluation of the enantioseparation capability of the novel chiral selector clindamycin phosphate towards basic drugs by micellar electrokinetic chromatography // J. Chromatogr. A. 2010. V.1217. P.1806−12.
- Huang, X., Wang, Q., Huang, B. Preparation and evaluation of stable coating for capillary electrophoresis using coupled chitosan as coated modifier // Talanta. 2006. V.69. P.463−8.
- Liu, Z., Otsuka, K., Terabe, S. Chiral separation by open tubular capillary electrochromatography with adsorbed avidin as a stationary phase // J. Sep. Sci. 2001. V.24. P. 17−26.
- Giibitz, G., Schmid, M.G. Recent advances in chiral separation principles in capillary electrophoresis and capillary electrochromatography // Electrophoresis. 2004. V.23. P.3981−96.
- Du, Y.X., Honda, S., Taga, A., Liu, W.Y., Suzuki, S. A novel polybrene/chondroitin sulfate C double coated capillary and its application in capillary electrophoresis // Electrophoresis. 2002. V.23. P.456−61.
- Du, Y., Taga, A., Suzuki, S., Liu, W., Honda, S. Colominic acid: a novel chiral selector for capillary electrophoresis of basic drugs // J. Chromatogr. A. 2002. V.962. P.221−31.
- Lu, H.-J., Ou, Q.-Y. Preparation and evaluation of open tubular electrochromatography column with derivated polysiloxane as stationary phase // Chem. J. Chin. Univ. 2002. V.23. P.30−3.
- Wang, Y., Zeng, Z., Guan, N., Cheng, J. Sol-gel technique for the preparation of cyclodextrin derivative stationary phase in open-tubular capillary electrochromatography // Electrophoresis. 2001. V.22. P.2167−72.
- Valtcheva, L., Mohammad, J., Pettersson, G., Hjerten, S. Chiral separation of beta-blockers by high-performance capillary electrophoresis based on nonimmobilized cellulase as enantioselective protein//J. Chromatogr. 1993. V.638. P.263−7.
- Poinsot, V., Bayle, C., Couderc, F. Recent advances in amino acid analysis by capillary electrophoresis // Electrophoresis. 2003. V.24. P.4047−62.
- Gong, X.Y., Kuban, P., Scholer, A., Hauser, P.C. Determination of a-hydroxybutyric acid in clinical samples using capillary electrophoresis with contactless conductivity detection // J. Chromatogr. A. 2008. V.1213. P. 100−4.
- Pormsila, W., Gong, X.Y., Hauser, P.C. Determination of the enantiomers of a -hydroxy-and a-amino acids in capillary electrophoresis with contactless conductivity detection // Electrophoresis. 2010. V.31. P.2044−8.
- Ali, I., Kumerer, K., Aboul-Enein, H.Y. Mechanistic principles in chiral separations using liquid chromatography and capillary electrophoresis // Chromatographic 2006. V.63. P.295−307.
- Armstrong, D.W., Nair, U.B. Capillary electrophoretic enantioseparations using macrocyclic antibiotics as chiral selectors // Electrophoresis. 1997. V.18. P.2331−42.
- Ward, T.J., Farris, III A.B., Woodling, K. Synergistic chiral separations using the glycopeptides ristocetin A and vancomycin // J. Biochem. Biophys. Methods. 2001. V.48. P. 16 374.
- Trelli-Seifert, L.A., Risley, D.S. Capillary Electrophoretic Enantiomeric Separations of Nonsteroidal Antiinflammatory Compounds Using the Macrocyclic Antibiotic Actaplanin A and 2-Methoxyethanol//J. Liq. Chrom. & Rel. Technol. 1998. V.21. P.299−313.
- Maier, V., Petr, J., Knob, R., Horakova, J., Sevcik, J. Electrokinetic partial filling technique as a powerful tool for enantiomeric separation of DL-lactic acid by CE with contactless conductivity detection // Electrophoresis. 2007. V.28. P.1815−22.
- Hu, C.-q., Hong, J.-w. Investigation on the chiral recognition site of enantioselective separation of ofloxacin by capillary electrophoresis using vancomycin as a chiral selector // Acta Pharm Sin. 2009. V.44. P.905−10.
- Gao, W., Kang, J. Separation of atropisomers of anti-hepatitis drug dimethyl diphenyl bicarboxilate analogues by capillary electrophoresis with vancomycin as the chiral selector // J. Chromatogr. A. 2006. V.1108. P.145−8.
- Fang, N., Zhang, H., Li, H.-W., Yeung, E.S. Mobility-based wall adsorption isotherms for comparing capillary electrophoresis with single-molecule observations // Anal. Chem. 2007. V.79. P.6047−54.
- Berdnikova, T.F., Shashkov, A.S., Katrukha, G.S., Lapchinskaya, O.A., Yurkevicha, N.V., Grachev, A.A., Nifant’ev, N.E. The structure of antibiotic eremomycin В // Rus. J. Bioorg. Chem. 2009. V.53. P.497−503.
- Gause, G.F., Brazhnikova, M.G., Lomakina, N.N., Berdnikova, T.F., Fedorova, G.B., Tokareva, — N.L., Borisova, V.N., Batta, G.Y. Eremomycin new glycopeptide antibiotic: Chemical properties and structure // J. Antibiot. 1989. V.XLII. P.1790−9.
- Ward, T.J., Farris, III A.B. Chiral separations using the macrocyclic antibiotics: a review //J. Chromatogr. A. 2001. V.906. P.73−89.
- Good, N., Winget, G., Winter, W., Connolly, Т., Izawa, S., Singh, R. Hydrogen Ion Buffers for Biological Research // Biochemistry. 1966. V.5. P.466−77.
- Буданова, Н.Ю., Шаповалова, E.H., Шпнгун, О. А. Изучение возможности использования хитозана в капиллярном электрофорезе // Вестн. Моск. ун-та. Сер. 2. Химия. 2006. V.47. Р. 177−81.
- Sun, P., Landman, A., Hartwick, R.A. Chitosan coated capillary with reversed electroosmotic flow in capillary electrophoresis for the separation of basic drugs and proteins // J. Microcol. SeP.1994. V.6. P.403−7.
- Боголицын, К.Г., Резников, В.М. Химия сульфитных методов делигнификации древесины. М.: Экология, 1994. 289 с.
- Hamoudova, R., Pospisilova, M. Determination of ibuprofen and flurbiprofen in pharmaceuticals by capillary zone electrophoresis // J. Pharm. Biomed. Anal. 2006. V.41. P.1463−7.
- Blanco, M., Coello, J., Iturriaga, H., Maspoch, S., Perez-Maseda, C. Chiral and nonchiral determination of ketoprofen in pharmaceuticals by capillary zone electrophoresis // J. Chromatogr. A. 1998. V.799. P.301−7.