Adsorption of mandelic acid enantiomers on chiral stationary phase with grafted antibiotic eremomycin: The effect of the eluent pH

References

• Felinger, A.; Cavazzini, A.; Guiochon, G. Numerical Determination of the Competitive Isotherm of Enantiomers. J. Chromatogr. A. 2003, 986, 207–225. DOI: 10.1016/S0021-9673(02)01919-2.
   PubMed Web of Science ®Google Scholar
• Guiochon, G.; Felinger, A.; Katti, A. M.; Shirazi, S. G. Fundamentals of Preparative and Nonlinear Chromatography, 2nd ed.; Academic Press: Boston, MA, 2006.
   Google Scholar
• Arnell, R.; Forssén, P.; Fornstedt, T. Tuneable Peak Deformations in Chiral Liquid Chromatography. Anal. Chem. 2007, 79, 5838–5847. DOI: 10.1021/ac062330t.
   PubMed Web of Science ®Google Scholar
• Forssén, P.; Arnell, R.; Kaspereit, M.; Seidel-Morgenstern, A.; Fornstedt, T. Effects of a Strongly Adsorbed Additive on Process Performance in Chiral Preparative Chromatography. J. Chromatogr. A. 2008, 1212, 89–97. DOI: 10.1016/j.chroma.2008.10.040.
   PubMed Web of Science ®Google Scholar
• Reshetova, E. N.; Asnin, L. D. Adsorption of Ibuprofen Enantiomers on a Chiral Stationary Phase with a Grafted Antibiotic Eremomycin. Russ. J. Phys. Chem. 2015, 89, 275–281. DOI: 10.1134/S0036024415020259.
   Web of Science ®Google Scholar
• Åsberg, D.; Leśko, M.; Samuelsson, J.; Karlsson, A.; Kaczmarski, K.; Fornstedt, T. Combining Chemometric Models with Adsorption Isotherm Measurements to Study Omeprazole in RP-LC. Chromatographia 2016, 79, 1283–1291. DOI: 10.1007/s10337-016-3151-8.
   PubMed Web of Science ®Google Scholar
• Kazakevich, Y. V. High-Performance Liquid Chromatography Retention Mechanisms and Their Mathematical Descriptions. J. Chromatogr. A. 2006, 1126, 232–243. DOI: 10.1016/j.chroma.2006.05.022.
   PubMed Web of Science ®Google Scholar
• Gritti, F.; Guiochon, G. Effect of the Ionic Strength of Salts on Retention and Overloading Behavior of Ionizable Compounds in Reversedphase Liquid Chromatography. I. XTerra-C18. J. Chromatogr. A. 2004, 1033, 43–55. DOI: 10.1016/j.chroma.2004.01.027.
   PubMed Web of Science ®Google Scholar
• Gritti, F.; Guiochon, G. Peak Shapes of Acids and Bases under Overloaded Conditions in Reversed-Phase Liquid Chromatography, with Weakly Buffered Mobile Phases of Various pH: A Thermodynamic Interpretation. J. Chromatogr. A. 2009, 1216, 63–78. DOI: 10.1016/j.chroma.2008.11.020.
   PubMed Web of Science ®Google Scholar
• Asnin, L.; Kaczmarski, K.; Guiochon, G. Features of the Adsorption of Naproxen Enantiomers on Weak Chiral Anion-Exchangers in Nonlinear Chromatography. J. Chromatogr. A. 2008, 1192, 62–73. DOI: 10.1016/j.chroma.2008.03.023.
   PubMed Web of Science ®Google Scholar
• Asnin, L.; Kaczmarski, K.; Guiochon, G. The Adsorption of Naproxen Enantiomers on the Chiral Stationary Phase Whelk-O1 under Reversed-Phase Conditions: The Effect of Buffer Composition. J. Chromatography A. 2010, 1217, 7055–7064. DOI: 10.1016/j.chroma.2010.08.073.
   PubMed Web of Science ®Google Scholar
• Gritti, F.; Guiochon, G. Adsorption Mechanism of Acids and Bases in Reversed-Phase Liquid Chromatography in Weak Buffered Mobile Phases Designed for Liquid Chromatography/Mass Spectrometry. J. Chromatogr. A. 2009, 1216, 1776–1788. DOI: 10.1016/j.chroma.2008.10.064.
   PubMed Web of Science ®Google Scholar
• Gritti, F.; Guiochon, G. Band Profiles of Reacting Acido-Basic Compounds with Water-Methanol Eluents at Different SWpHs and Ionic Strengths in Reversed-Phase Liquid Chromatography. J. Chromatogr. A. 2009, 1216, 3175–3184. DOI: 10.1016/j.chroma.2009.02.013.
   PubMedGoogle Scholar
• Asnin, L. D.; Guiochon, G. Retention of Naproxen Enantiomers on the Chiral Stationary Phase Whelk-O1 under Reversed-Phase Conditions. A Reconsideration of the Adsorption Mechanism in the Light of New Experimental Data. J. Chromatogr. A. 2010, 1217, 1709–1711. DOI: 10.1016/j.chroma.2010.01.017.
   PubMed Web of Science ®Google Scholar
• Reshetova, E. N.; Asnin, L. D.; Kachmarsky, K. Effect of Secondary Equilibria on the Adsorption of Ibuprofen Enantiomers on a Chiral Stationary Phase with a Grafted Antibiotic Eremomycin. Russ. J. Phys. Chem. 2018, 92, 361–367. DOI: 10.1134/S0036024418010223.
   Web of Science ®Google Scholar
• Gritti, F.; Guiochon, G. Adsorption Behavior of the Three Species of the Biprotic Peptide Phe-Ala onto an End-Capped C18-Bonded Organic/Inorganic Hybrid Stationary Phase. Anal. Chem. 2009, 81, 9871–9884. DOI: 10.1021/ac902027t.
   PubMed Web of Science ®Google Scholar
• Berthod, A.; Qiu, H. X.; Staroverov, S. M.; Kuznestov, M. A.; Armstrong, D. W. Chiral Recognition with Macrocyclic Glycopeptides: mechanisms and Applications. In Chiral Recognition in Separation Methods: Mechanisms and Applications; Berthod, A., ed. Springer Berlin Heidelberg: Berlin, Heidelberg, 2010.
   Google Scholar
• Reshetova, E. N.; Asnin, L. D. Effect of the Ionic Composition of a Mobile Phase on the Chromatographic Retention of Profen Enantiomers on a Chiral Adsorbent with Grafted Eremomycin Antibiotic. Russ. J. Phys. Chem. 2011, 85, 1434–1439. DOI: 10.1134/S0036024411080280.
   Web of Science ®Google Scholar
• Reshetova, E. Chromatographic Retention and Thermodynamics of the Adsorption of α-Phenylcarboxylic Acid Enantiomers on a Chiral Stationary Phase with a Grafted Antibiotic Eremomycin: Effect of Eluent pH. J. Liq. Chromatogr. Relat. Technol. 2016, 39, 145–153. DOI: 10.1080/10826076.2015.1137004.
   Web of Science ®Google Scholar
• Poplewska, I.; Kramarz, R.; Piątkowski, W.; Seidel-Morgenstern, A.; Antos, D. Influence of Preferential Adsorption of Mobile Phase on Retention Behavior of Amino Acids on the Teicoplanin Chiral Selector. J. Chromatography A. 2007, 1173, 58–70. DOI: 10.1016/j.chroma.2007.09.076.
   PubMed Web of Science ®Google Scholar
• Staroverov, S. M.; Kuznetsov, M. A.; Nesterenko, P. N.; Vasiarov, G. G.; Katrukha, G. S.; Fedorova, G. B. New Chiral Stationary Phase with Macrocyclic Glycopeptide Antibiotic Eremomycin Chemically Bonded to Silica. J. Chromatogr. A. 2006, 1108, 263–267. DOI: 10.1016/j.chroma.2006.01.073.
   PubMed Web of Science ®Google Scholar
• Kuznetsov, M. A.; Nesterenko, P. N.; Vasiyarov, G. G.; Staroverov, S. M. High-Performance Liquid Chromatography of α-Amino Acid Enantiomers on Eremomycin-Modified Silica. J. Anal. Chem. 2008, 63, 57–64. DOI: 10.1134/S1061934808010115.
   Web of Science ®Google Scholar
• Natykan, A. A.; Sycheva, K.; Yu Chernobrovkin, M. G.; Shapovalova, E. N.; Shpigun, O. A. Chromatographic Determination of Amino Acids and Their Optical Isomers Using the Nautilus-E Column. Zavod. Lab. Materials Diagnostics 2011, 77, 18–21. [in Russian].
   Google Scholar
• Reshetova, E. N.; Asnin, L. D. The Chromatographic Behavior and Thermodynamic Characteristics of Adsorption of Profen Enantiomers on Silica Gel with Grafted Eremomycin Antibiotic. Russ. J. Phys. Chem. 2009, 83, 547–551. DOI: 10.1134/S0036024409040062.
   Web of Science ®Google Scholar
• Reshetova, E. N.; Gogolishvili, O. Sh. Adsorption of Mandelic Acid Enantiomers on a Chiral Stationary Phase with a Grafted Antibiotic Eremomycin. J. Liq. Chromatogr. Relat. Technol. 2018, 41, 561–571. DOI: 10.1080/10826076.2018.1459305.
   Web of Science ®Google Scholar
• Ilisz, I.; Berkecz, R.; Péter, A. Retention Mechanism of High-Performance Liquid Chromatographic Enantioseparation on Macrocyclic Glycopeptide-Based Chiral Stationary Phases. J. Chromatogr. A. 2009, 1216, 1845–1860. DOI: 10.1016/j.chroma.2008.08.041.
   PubMed Web of Science ®Google Scholar
• Petrusevska, K.; Kuznetsov, M. A.; Gedicke, K.; Meshko, V.; Staroverov, S. M.; Seidel-Morgenstern, A. Chromatographic Enantioseparation of Amino Acids Using a New Chiral Stationary Phase Based on a Macrocyclic Glycopeptide Antibiotic. J. Sep. Sci. 2006, 29, 1447–1457. DOI: 10.1002/jssc.200600036.
   PubMed Web of Science ®Google Scholar
• Nair, U. B.; Chang, S. S. C.; Armstrong, D. W.; Rawjee, Y. Y.; Eggleston, D. S.; McArdle, J. V. Elucidation of Vancomycin's Enantioselective Binding Site Using Its Copper Complex. Chirality 1996, 8, 590–595. DOI: 10.1002/(SICI)1520-636X(1996)8:8<590::AID-CHIR9>3.0.CO;2-D.
   Web of Science ®Google Scholar
• Kuznetsov MA (2008) Enantioselective sorbents with immobilized macrocyclic glycopeptide antibiotics. PhD thesis. Moscow. p 131. The Russian State Library (In Russian). https://www.rsl.ru
   Google Scholar
• D’Acquarica, I.; Gasparrini, F.; Misiti, D.; Pierini, M.; Villani, C. HPLC Chiral Stationary Phases Containing Macrocyclic Antibiotics: practical Aspects and Recognition Mechanisms. In Adv. Chromatogr; Grushka, E., Grinberg, N., Eds.; CRC Press: Boca-Raton, FL, 2008; pp. 109–173; , Vol. 46.
   Google Scholar
• Boehm, R. E.; Martire, D. E.; Armstrong, D. W. Theoretical Considerations Concerning the Separation of Enantiomeric Solutes by Liquid Chromatography. Anal. Chem. 1988, 60, 522–528. DOI: 10.1021/ac00157a006.
   PubMed Web of Science ®Google Scholar
• Jandera, P.; Bunčeková, S.; Mihlbachler, K.; Guiochon, G.; Bačkovská, V.; Planeta, J. Fitting Adsorption Isotherms to the Distribution Data Determined Using Packed Micro-Columns for High-Performance Liquid Chromatography. J. Chromatogr. A 2001, 925, 19–29. DOI: 10.1016/S0021-9673(01)01002-0.
   PubMed Web of Science ®Google Scholar
• Jander, P.; Backovská, V.; Felinger, A. Analysis of the Band Profiles of the Enantiomers of Phenylglycine in Liquid Chromatography on Bonded Teicoplanin Columns Using the Stochastic Theory of Chromatography. J. Chromatogr. A. 2001, 919, 67–77. DOI: 10.1016/s0021-9673(01)00783-x.
   PubMed Web of Science ®Google Scholar
• Kaspereit, M.; Jandera, P.; Škavrada, M.; Seidel-Morgenstern, A. Impact of Adsorption Isotherm Parameters on the Performance of Enantioseparation Using Simulated Moving Bed Chromatography. J. Chromatogr. A. 2002, 944, 249–262. DOI: 10.1016/s0021-9673(01)01341-3.
   PubMed Web of Science ®Google Scholar
• Cavazzini, A.; Pasti, L.; Dondi, F.; Finessi, M.; Costa, V.; Gasparrini, F.; Ciogli, A.; Bedani, F. Binding of Dipeptides and Amino Acids to Teicoplanin Chiral Stationary Phase: Apparent Homogeneity of Some Heterogeneous Systems. Anal. Chem. 2009, 81, 6735–6743. DOI: 10.1021/ac900677f.
   PubMed Web of Science ®Google Scholar
• Jandera, P.; Škavrada, M.; Klemmová, K.; Bačkovská, V.; Guiochon, G. Effect of the Mobile Phase on the Retention Behaviour of Optical Isomers of Carboxylic Acids and Amino Acids in Liquid Chromatography on Bonded Teicoplanin Columns. J. Chromatogr. A. 2001, 917, 123–133. DOI: 10.1016/s0021-9673(01)00701-4.
   PubMed Web of Science ®Google Scholar
• Zhang, L.; Gedicke, K.; Kuznetsov, M. A.; Staroverov, S. M.; Seidel-Morgenstern, A. Application of an Eremomycin-Chiral Stationary Phase for the Separation of DL-Methionine Using Simulated Moving Bed Technology. J. Chromatogr. A. 2007, 1162, 90–96. DOI: 10.1016/j.chroma.2007.04.033.
   PubMed Web of Science ®Google Scholar
• Charton, F.; Bailly, M.; Guiochon, G. Recycling in Preparative Liquid Chromatography. J. Chromatogr. A. 1994, 687, 13–31. DOI: 10.1016/0021-9673(94)00728-4.
   Web of Science ®Google Scholar
• Fornstedt, T.; Sajonz, P.; Guiochon, G. A Closer Study of Chiral Retention Mechanisms. Chirality 1998, 10, 375–381. DOI: 10.1002/(SICI)1520-636X(1998)10:5<375::AID-CHIR3>3.0.CO;2-5.
   Web of Science ®Google Scholar
• Bates, R. G. National Bureau of Standards. Determination of pH. Theory and Practice; John Wiley & Sons Inc: New York, London, Sydney, 1964.
   Google Scholar
• Canals, I.; Oumada, F. Z.; Rosés, M.; Bosch, E. Retention of Ionizable Compounds on HPLC. 6. pH Measurements with the Glass Electrode in Methanol–Water Mixtures. J. Chromatogr. 2001, 911, 191–202. DOI: 10.1016/S0021-9673(00)01271-1.
   PubMed Web of Science ®Google Scholar
• Canals, I.; Portal, J. A.; Bosch, E.; Rosés, M. Retention of Ionizable Compounds on HPLC. 4. Mobile-Phase pH Measurement in Methanol/Water. Anal. Chem. 2000, 72, 1802–1809. DOI: 10.1021/ac990943i.
   PubMed Web of Science ®Google Scholar
• Oumada, F. Z.; Ràfols, C.; Rosés, M.; Bosch, E.; et. al. Chromatographic Determination of Aqueous Dissociation Constants of Some Water-Insoluble Nonsteroidal Antiinflammatory Drugs. J. Pharm. Sci. 2002, 91, 991–999. DOI: 10.1002/jps.10096.
   PubMed Web of Science ®Google Scholar
• Nikitina, Y. K.; Ali, I.; Asnin, L. D. Adsorption of Aqueous Organic Mixtures on a Chiral Stationary Phase with Bound Antibiotic Eremomycin. J. Chromatogr. A. 2014, 1363, 71–78. DOI: 10.1016/j.chroma.2014.08.062.
   PubMed Web of Science ®Google Scholar
• Lanin, S. N.; Ledenkova, M. Y.; Nikitin, Y. S. Calculation of Sorption Isotherms from the Retention Parameters in High-Performance Liquid Chromatography. Mendeleev. Commun. 2000, 10, 37–38. DOI: 10.1070/MC2000v010n01ABEH001191.
   Google Scholar
• Kaczmarski, K. Estimation of Adsorption Isotherm Parameters with Inverse Method: Possible Problems. J. Chromatography A 2007, 1176, 57–68. DOI: 10.1016/j.chroma.2007.08.005.
   PubMed Web of Science ®Google Scholar
• Guiochon, G. Preparative Liquid Chromatography. J. Chromatogr. A. 2002, 965, 129–161. DOI: 10.1016/s0021-9673(01)01471-6.
   PubMed Web of Science ®Google Scholar
• Rachinskii, V. V. An Introduction to the General Theory of Sorptional and Chromatography Dynamics; Nauka: Moscow, 1964. [in Russian]
   Google Scholar
• Danckwerts, P. W. Continuous Flow Systems: Distribution of Residence Times. Chem. Eng. Sci. 1953, 2, 1–13. DOI: 10.1016/0009-2509(53)80001-1.
   Web of Science ®Google Scholar
• Kaczmarski, K.; Mazzotti, M.; Storti, G.; Morbidelli, M. Modeling Fixed-Bed Adsorption Columns through Orthogonal Collocations on Moving Finite Elements. Comput. Chem. Eng. 1997, 21, 641–660. DOI: 10.1016/S0098-1354(96)00300-6.
   Web of Science ®Google Scholar
• Kaczmarski, K. Use of Orthogonal Collocation on Finite Elements with Moving Boundaries in the Simulation of Non-Linear Multicomponent Chromatography. Influence of Fluid Velocity Variation on Retention Time in LC and HPLC. Comput. Chem. Eng. 1996, 20, 49–64. DOI: 10.1016/0098-1354(95)00004-L.
   Web of Science ®Google Scholar
• Kaczmarski, K.; Antos, D. Calculation of Chromatographic Band Profiles with an Implicit Isotherm. J. Chromatogr. A. 1999, 862, 1–16. DOI: 10.1016/s0021-9673(99)00901-2.
   PubMed Web of Science ®Google Scholar
• Fletcher, R. A Modified Marquardt Sub-Routine for Non-Linear Least Squares. Atomic Energy Research Establishment report R6799. 27 p. Harwell 1971.
   Google Scholar
• Prokhorova, A. F.; Shapovalova, E. N.; Shpak, A. V.; Staroverov, S. M.; Shpigun, O. A. Enantiorecognition of Profens by Capillary Electrophoresis Using a Novel Chiral Selector Eremomycin. J. Chromatogr. A. 2009, 1216, 3674–3677. DOI: 10.1016/j.chroma.2009.02.017.
   PubMed Web of Science ®Google Scholar
• Kiselev, A. V.; Johansen, A. V.; Sakodynsky, K. I.; Sakharov, V. M.; Yashin, J. I.; Karnaukhov, A. P.; Buyanova, N. E.; Kurkchi, G. A. Physic-Chemical Application  of Gas Chromatography; Chemistry: Moscow, 1973. [in Russian]
   Google Scholar
• Chen, Y.; Kele, M.; Quiñones, I.; Sellergren, B.; Guiochon, G. Influence of the pH on the Behavior of an Imprinted Polymeric Stationary Phase — Supporting Evidence for a Binding Site Model. J. Chromatogr. A. 2001, 927, 1–17. DOI: 10.1016/S0021-9673(01)01019-6.
   PubMed Web of Science ®Google Scholar
• Asnin, L.; Kaczmarski, K.; Felinger, A.; Gritti, F.; Guiochon, G. Adsorption of the Enantiomers of 3-Chloro-1-Phenyl-Propanol on Silica-Bonded Chiral Quinidine Carbamate. J. Chromatogr. A. 2006, 1101, 158–170. DOI: 10.1016/j.chroma.2005.09.078.
   PubMed Web of Science ®Google Scholar
• Bechtold, M.; Heinemann, M.; Panke, S. Suitability of Teicoplanin–Aglycone Bonded Stationary Phase for Simulated Moving Bed Enantioseparation of Racemic Amino Acids Employing Composition-Constrained Eluents. J. Chromatography A. 2006, 1113, 167–176. DOI: 10.1016/j.chroma.2006.02.007.
   PubMed Web of Science ®Google Scholar
• Asnin, L. Adsorption Models in Chiral Chromatography. J. Chromatogr. A. 2012, 1269, 3–25. DOI: 10.1016/j.chroma.2012.08.096.
   PubMed Web of Science ®Google Scholar
• Cavazzini, A.; Felinge, A.; Kaczmars, K.; Szabelsk, P.; Guiochon, G. Study of the Adsorption Equilibria of the Enantiomers of 1-Phenyl-1-Propanol on Cellulose Tribenzoate Using a Microbore Column. J. Chromatogr. A. 2002, 953, 55–66. DOI: 10.1016/s0021-9673(02)00150-4.
   PubMed Web of Science ®Google Scholar
• Fornstedt, T.; Götmar, G.; Andersson, M.; Guiochon, G. Dependence on the Mobile-Phase pH of the Adsorption Behavior of Propranolol Enantiomers on a Cellulase Protein Used as the Chiral Selector. J. Am. Chem. Soc. 1999, 121, 1164–1174.
   Web of Science ®Google Scholar
• Asnin, L. D.; Cavazzini, A.; Marchetti, N. Solute-Stationary Phase Interaction in Chiral Chromatography. Adv. Chromatogr. 2016, 53, 1–73.
   Web of Science ®Google Scholar
• Götmar, G.; Albareda, N. R.; Fomstedt, T. Investigation of the Heterogeneous Adsorption Behavior of Selected Enantiomers on Immobilized Alpha1-Acid Glycoprotein. Anal. Chem. 2002, 74, 2950–2959. DOI: 10.1021/ac011182y.
   PubMed Web of Science ®Google Scholar
• Asnin, L.; Gritti, F.; Kaczmarski, K.; Guiochon, G. () Features of the Adsorption of Naproxen on the Chiral Stationary Phase (S,S)-Whelk-O1 under Reversed-Phase Conditions. J. Chromatogr. A. 2010, 1217, 264–275. DOI: 10.1016/j.chroma.2009.11.039.
   PubMed Web of Science ®Google Scholar