Some insights on retention and selectivity for hydrophilic interaction chromatography

Journal of Liquid Chromatography and Related Technologies

Volumn 32, Issue 5, 2009, Pages 628-646

  Yang, Mei ^a   Thompson, Richard ^b   Hall, Gene ^c  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NOVARTIS PHARMA AG   (Switzerland)

^c RUTGERS UNIVERSITY   (United States)

Author keywords

Amino acids; Hydrophilic interaction chromatography; Polar compounds

Indexed keywords

ACETONITRILE; AMINATION; AMINES; AMINO ACIDS; CHROMATOGRAPHIC ANALYSIS; ION EXCHANGE; LIQUID CHROMATOGRAPHY; ORGANIC ACIDS; ORGANIC SOLVENTS; PHOSPHORIC ACID; SILICA;

AQUEOUS MOBILE PHASE; ELECTROSTATIC INTERACTIONS; HYDROPHILIC INTERACTION CHROMATOGRAPHY; LIPOPHILICITY; PHARMACEUTICAL COMPOUNDS; POLAR COMPOUNDS; PROTONATED SITES; PURE SILICAS; RETENTION MECHANISMS; STATIONARY PHASE; STERIC HINDRANCES; VERSATILE TOOLS;

HYDROPHILICITY;

ACETONITRILE; AMINO ACID; AMPHOLYTE; PHOSPHORIC ACID; PYRIDINE; SILICON DIOXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; ELECTRICITY; HYDROPHILIC INTERACTION CHROMATOGRAPHY; ION EXCHANGE; LIPOPHILICITY; PKA; PROTEIN STRUCTURE;

EID: 61649107878     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826070802711048     Document Type: Article

References (44)

1. Nawrocki, J. The silanol group and its role in liquid chromatography. J. Chromatogr. A. 1997, 779, 29-71.
2. Law, B. Use of silica with reversed-phase type eluents for the analysis of basic drugs and metabolites. Trends Anal. Chem. 1990, 9, 31-36.
3. Einarsson, S.; Josefsson, B.; Lagerkvist, S. Separation of basic drugs by high-performance liquid chromatography on a silica column using a methanol-ethylenediamine buffer. J. Chromatogr. 1983, 280, 609-618.
4. Roturier, J.M.; Bars, D.L.; Gripon, J.C. Separation and identification of hydrophilic peptides in dairy products using FMOC derivatization. J. Chromatogr. A. 1995, 696, 209-217.
5. Hemstrom, P.; Irgum, K. Hydrophilic interaction chromatography. J. Sep. Sci. 2006, 29, 1784-1821.
6. Alpert, A.J. Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds. J. Chromatogr. 1990, 499, 177-196.
7. Law, B. Analysis of basic compounds on a silica column with an aqueous methanol eluent: The use of quantitative structure-retention relationships in metabolite identification. J. Chromatogr. 1987, 407, 1-18.
8. Binder, S.R. In: Analysis of Addictive and Misused Drugs; Adamovics, J.A., Ed.; Marcel Dekker, Inc.: New York. 1995, 133.
9. Schlichtherle-Cerny, H.; Affolter, M.; Cerny, C. Hydrophilic interaction liquid chromatography coupled to electrospray mass spectrometry of small polar compounds in food analysis. Anal. Chem. 2003, 75, 2349-2354.
10. Churms, S.C. Recent progress in carbohydrate separation by high-performance liquid chromatography based on hydrophilic interaction. J. Chromatogr. A. 1996, 720, 75-91.
11. Oyler, A.R.; Armmstrong, B.L.; Cha, J.Y.; Zhou, M.X.; Yang, Q.; Robinson, R.I.; Dunphy, R.; Burinsky, D.J. Hydrophilic interaction chromatography on amino-silica phases complements reversed-phase high-performance liquid chromatography and capillary electrophoresis for peptide analysis. J. Chromatogr. A. 1996, 724, 378-383.
12. Tanaka, H.; Zhou, X.J.; Masayoshi, O. Characterization of a novel diol column for high-performance liquid chromatography. J. Chromatogr A. 2003, 987, 119-125.
13. Strege, M.A. Hydrophilic interaction chromatography-electrospray mass spectrometry analysis of polar compounds for natural product drug discovery. Anal. Chem. 1998, 70, 2439-2445.
14. Strege, M.A.; Stevenson, S.; Lawrence, S.M. Mixed-Mode Anion-Cation Exchange/Hydrophilic Interaction Liquid chromatography-electrospray mass spectrometry as an alternative to reversed phase for small molecule drug discovery. Anal. Chem. 2000, 72, 4629-4633.
15. Guo, Y.; Huang, A. A HILIC method for the analysis of tromethamine as the counter ion in an investigational pharmaceutical salt. J. Pharm. Biomed. Anal. 2003, 31, 1191-1201.
16. Li, R.; Huang, J. Chromatographic behavior of epirubicin and its analogues on high-purity silica in hydrophilic interaction chromatography. J. Chromatogr. A. 2004, 1041, 163-169.
17. Dallet, P.; Labat, L.; Kummer, E.; Dubost, J.P. Determination of urea, allantoin and lysine pyroglutamate in cosmetic samples by hydrophilic interaction chromatography. J. Chromatogr. B. 2000, 742, 447-452.
18. Bidlingmeyer, B.A.; Del Rios, J.K.; Korpi, J. Separation of organic amine compounds on silica gel with reversed-phase eluents. Anal. Chem. 1982, 54, 442-447.
19. Cox, G.B.; Stout, R.W. Study of the retention mechanism for basic compounds on silica under "pseudo-reversed-phase" conditions. J. Chromatogr. 1987, 384, 315-336.
20. Marcus, Y.; Migron, Y. Polarity, hydrogen bonding, and structure of mixtures of water and cyanomethane. J. Phys. Chem. 1991, 95, 400-406.
21. Katz, E.D.; Lochmuller, C.H.; Scott, R.P.W. Methanol-water association and its effect on solute retention in liquid chromatography. Anal. Chem. 1989, 61, 349-355.
22. McCalley, D.V. Influence of analyte stereochemistry and basicity on peak shape of basic compounds in high-performance liquid chromatography with reversed-phase columns, using pyridine and alkyl-substituted derivatives as probe compounds. J. Chromatogr. A. 1994, 664, 139-147.
23. Barbosa, J.; Beltran, J.; Sanz-Nebot, V. Ionization constants of pH reference materials in acetonitrile-water mixtures up to 70% (w/w). Anal. Chim. Acta. 1994, 288, 271-278.
24. Barbosa, J.; Sanz-Nebot, V. Preferential solvation in acetonitrile-water mixtures: Relationship between solvatochromic parameters and standard pH values. J. Chem. Soc. Faraday Trans. 1994, 90, 3287-3292.
25. Roses, M.; Canals, I.; Alleman, H.; Siigur, K.; Bosch, E. Retention of ionizable compounds on HPLC. 2. Effect of pH, ionic strength, and mobile phase composition on the retention of weak acids. Anal. Chem. 1996, 68, 4094-4100.
26. Bosch, E.; Bou, P.; Alleman, H.; Roses, M. Retention of Ionizable Compounds on HPLC. pH Scale in Methanol-Water and the pK and pH Values of Buffers. Anal. Chem. 1996, 68, 3651-3657.
27. Sykora, D.; Tesarova, E.; Popl, M. Interactions of basic compounds in reversed-phase high-performance liquid chromatography influence of sorbent character, mobile phase composition, and pH on retention of basic compounds, J. Chromatogr. A. 1997, 758, 37-51.
28. Canals, I.; Oumada, F.; Roses, M.; Bosch, E. Retention of ionizable compounds on HPLC. 6. pH measurements with the glass electrode in methanol-water mixtures. J. Chromatogr. A 2001, 911, 191-202.
29. LoBrutto, R.; Jones, A.; Kazakevich, Y.; McNair, H. Effect of the eluent pH and acidic modifiers in high-performance liquid chromatography retention of basic analytes. J. Chromatogr. A 2001, 913, 173-187.
30. Espinosa, S.; Bosch, E.; Roses, M. Retention of Ionizable Compounds on HPLC. 12. The Properties of liquid chromatography buffers in acetonitrile-water mobile phases that influence HPLC retention. Anal. Chem. 2002, 74, 3809-3818.
31. Espinosa, S.; Bosch, E.; Roses, M. Retention of ionizable compounds on HPLC. 14 Acid-base pK values in acetonitrile-water mobile phases. J. Chromatogr. A. 2002, 964, 55-66.
32. Subirats, X.; Bosch, E.; Roses, M. Retention of ionizable compounds onHPLC. 15. Estimation of the pH variation of aqueous buffers with the change of the acetonitrile fraction of the mobile phase. J. Chromatogr. A. 2004, 1059, 33-42.
33. Mendez, A.; Bosch, E.; Roses, M.; Neue, U. Comparison of the acidity of residual silanol groups in several liquid chromatography columns. J. Chromatogr. A. 2003, 986, 33-44.
34. Lide, D.R., Ed. CRC, Handbook of Chemistry and Physics, 85th Ed.; CRC Press: Boca Raton, FL, 2004.
35. Dean, J.A., Ed. Lange's Handbook of Chemistry, 14th Ed.; McGraw-Hill: New York, 1992.
36. The predicted values of pKa and log P were obtained using the ACD Lab 6.0 software (Advanced Chemistry Development, Inc., Toronto, Canada).
37. Sereda, T.J.; Mant, C.T.; Sonnichsen, F.D.; Hodges, R.S. Reversed-phase chromatography of synthetic amphipathic a-helical peptides as a model for ligand/receptor interactions Effect of changing hydrophobic environment on the relative hydrophilicity/hydrophobicity of amino acid side-chains. J. Chromatogr. A. 1994, 676, 139-153.
38. http://www.sigmaaldrich.com/Area-of Interest/Biochemicals/Peptide- Explorer/Key-Resources/Reference-Chart.html
39. Nakazato, A.; Kumagai, T.; Sakagami, K.; Yoshikawa, R.; Suzuki, Y.; Chaki, S.; Ito, H.; Taguchi, T.; Nakanishi, S.; Okuyama, S. Synthesis SARs, and pharmacological characterization of 2-amino-3- or 6-fluorobicyclo[3.1.0] hexane-2,6-dicarboxylic acid derivatives as potent, selective, and orally active group II metabotropic glutamate receptor agonists. J. Med. Chem. 2000, 43, 4893-4909.
40. Monn, J.; Valli, M.; Massey, S.; Wright, R.; Salhoff, C.; Johnson, B.; Howe, T.; Alt, C.; Rhodes, G.; Robey, R.; Griffey, K.; Tizzano, J.; Kallman, M.; Helton, D.; Schoepp, D. Design, synthesis, and pharmacological characterization of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740): A potent, selective, and orally active group 2 metabotropic glutamate receptor agonist possessing anticonvulsant and anxiolytic properties. J. Med. Chem. 1997, 40, 528-537.
41. Helton, D.; Tizzano, J.; Monn, J.; Schoepp, D.; Kallman, M. Anxiolytic and Side-Effect Profile of LY354740: A potent, highly selective, orally active agonist for group II metabotropic glutamate receptors. J. Pharmacol. Exp. Ther. 1998, 284, 651-660.
42. Monn, J.; Valli, M.; Massey, S.; Hansen, M.; Kress, T.; Wepsiec, J.; Harkness, A.; Grutsch, J.; Wright, R.; Johnson, B.; Andis, S.; Kingston, A.; Tomlinson, R.; Lewis, R.; Griffey, K.; Tizano, J.; Schoepp, D. Synthesis, pharmacological characterization, and molecular modeling of heterobicyclic amino acids related to (+)-2-aminobicyclo[3.1.0] hexane-2,6-dicarboxylic acid (LY354740): Identification of two new potent, selective and systemically active agonists for group II metabotropic glutamate receptors. J. Med. Chem. 1999, 42, 1027-1040.
43. Wickelgren, I. A new route to treating Schizophrenia? Science 1998, 281, 1264-1265.
44. Moghaddam, B.; Adams, B. Reversal of phencyclidine effects by a group II metabotropic glutamate receptor agonist in rats. Science. 1998, 281, 1349-1352.