Organic fluoro-containing compounds as chromatographic and elecrophoretic systems components
Keywords:
chromatography, fluorinated stationary phase, fluoroorganic compound, eluent additives.
Abstract
Fluorinated compounds application of as stationary phases, eluents and theirs modificators in
chromatography and capillary electrophoresis were described. Also fluorinated compounds employment
examples in natural objects and drugs analysis were considered.
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References
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perfluoroalkyl carboxylate, sulfonate, and sulfonamide isomers by liquid chromatographytandem
mass spectrometry // Anal. Chem., 2007, V. 79, P. 6455-6464.
2. B. J. Stockman. 2-Fluoro-ATP as a Versatile Tool for 19F NMR-based Activity
Screening // J. Am. Chem. Soc., 2008, V. 130, P. 5870-5871.
3. Clark, L. C., Jr. Gollan. Survival of mammals breathing organic liquids equilibrated
with oxygen at a atmospheric pressure // F. Science, V. 152, P. 1966, 1755-1756.
4. S. Purser, P.M. Moore, S. Swallow, V. Gouverneur. Fluorine in medicinal chemistry //
Chem. Soc. Rev., 2008, V. 37, P. 320–330.
5. Riess J. G., Le Blanc M. Solubility and transport phenomena in perfluorochemicals
relevant to blood substitution and other biomedical applications // Pure Appl. Chem., 1982,
V. 54, P. 2383-2406.
6. K. Müller, C. Faeh, F. Diederich. Fluorine in pharmaceuticals: Looking beyond
intuition // Science 2007, V. 317, P. 1881-1886.
7. Horváth, I. T. Solvents from nature // Green Chem, 2008, V. 10, P. 1024–1028.
8. Brittain S.M., Ficarro S.B., Brock A., Peters E.C. Enrichment and analysis of peptide
subsets using fluorous affinity tags and mass spectrometry // Nat Biotechnol, 2005, V. 23,
P. 463-468.
9. Lehmler H.-J. Perfluorocarbon compounds as vehicles for pulmonary drug delivery //
Expert Opin Drug Deliv., 2007, V.4, P. 247-262.
10. D. O`Hagan, D. B. Harper. Fluorine-containing natural products // J. Fluorine Chem.,
1999, V. 100, P. 127–133.
11. I. De Miguel, A. Roueche, D. Betbeder. Separation of dipalmitoyl phosphatidyl
choline, cholesterol and their degradation products by high-performance liquid
chromatography on a perfluorinated stationary bonded phase // J. Chromatogr. A, 1999, V. 840, P. 31-38.
12. S. Yang, L.F. Resotoko Kruk, M.G. Khaledi. Fluorinated bonded stationary phases in
micellar liquid chromatography // Journal of Chromatography A, 1994, V. 664, P. 1-11.
13. N. Xiao, Y. B. Yu. Separation of fluorinated amino acids and oligopeptides from their
non-fluorinated counterparts using high-performance liquid chromatography // Journal of
Fluorine Chemistry, 2010, V. 13, P. 439-445.
14. S.L. Richeimer, M.C. Kent, M.W. Bernart. Reversed-phase high-performance liquid
chromatograpic method using a pentafluorophenyl bonded phase for analysis of
tocopherols // J. Chromatogr. A, 1994, V. 667, P. 75-80.
15. D.S. Bell, H.M. Cramer, A.D. Jones. Rational method development strategies on a
fluorinated liquid chromatography stationary phase: mobile phase ion concentration and
temperature effects on the separation of ephedrine alkaloids // Journal of Chromatography
A, 2005, V. 1095, P. 113-118.
16. K. Valko, S. Espinosa, C.M. Du, E. Bosch, M. Roses, C. Bevan, M.H. Abraham.
Unique selectivity of perfluorinated stationary phases with 2,2,2-trifluoroethanol as organic
mobile phase modifier // J. Chromatogr. A, 2001, V. 933, P. 73-81.
17. J. Flieger. Application of perfluorinated acids as ion-pairing reagents for reversedphase
chromatography and retention-hydrophobicity relationships studies of selected β-
blockers // J. Chromatogr. A, 2010, V. 1217, P. 540-549.
18. F. Vernona and G.T. Edwardsa. Gas-liquid chromatography on fluorinated stationary
phases: I. Hydrocarbons and fluorocarbons // Journal of Chromatography A, 1975, V. 110,
P. 73-80.
19. F. Vernona and G.T. Edwardsa. Gas-liquid chromatography on fluorinated stationary
phases: II. Fluorinated compounds containing a functional group // Journal of
Chromatography A, 1975, V. 114, P. 87-93.
20. R. M. Pomavillea, C. F. Poole. Thermally stable, highly fluorinated stationary phases
for gas chromatography // Analytica Chimica Acta, 1987, V. 200, P. 151-169.
21. H. Shinohara, N. Asakura, S. Tsujimora. Gas Chromatographic Characteristics of
Polytrifluoromonochloroethylene Columns as applied to Analysis of Uranium
Hexafluoride and other Volatile Inorganic Fluorides // Journal of nuclear science and Tech.,
1966, V. 3, P. 373-378.
22. A.G. Hamlin, G. Iveson, T.R. Phillips. Analysis of volatile inorganic fluorides by gasliquid
chromatography // Anal. Chem. 1963, № 56, P. 2037-2040.
23. Т. М. Рощина, С. В. Глазкова, А. Д. Хрычева. Газохроматографическое
исследование свойств поверхности фторированного углерода // Вестн. Моск. Ун-та.
Серия 2. Химия, 2005, Т. 46, №1, С. 29-33.
24. Т. М. Рощина, С. В. Глазкова, А. Д. Хрычева, В.Г. Макотченко, М. Л. Пантюхин.
Исследование влияния фторрования на свойства поверхности углеродных
материаловметодом газовой хроматографии // Вестн. Моск. Ун-та. Серия 2. Химия,
2007, Т. 48, №2, С. 80-85.
25. T.M. Reed Ill. Gas-Liquid Partition Chromatography of Fluorocarbons // Anal.
Chem., 1958, V. 30, P. 221-228.
26. А.Н. Король, В.М. Сахаров. К вопросу избирательности фторсодержащих
неподвижных фаз в газовой хроматографии // Газовая хроматография, 1967, вып. 7,
С. 39-47.
27. В.В. Бражников, Л.И. Мосева, К.И. Сакодынский, В.А. Сокольский.
Модифицированный фторопластовый носитель // Газовая хроматография, 1969, вып.
8, С. 80-85.
28. H. Glatz, C. Blay, H. Engelhardt, W. Bannwarth. New fluorous reversed phase silica
gels for HPLC separations of perfluorinated compounds // Chromatographia, 2004, 59, № 9/10, P. 567-570.
29. M. P. Krafft, Fr. Jeannaux, M. Le Blanc, J. G. Riess, A. Berthod. Highly fluorinated
stationary phases for analysis of polyfluorinated solutes by reversed-phase highperformance
liquid chromatography // Anal. Chem., 1988, 60 (18), P. 1969–1972.
30. L. O. Healy, V. P. Owens, T. O`Mahony, S. Srijaranai, J. D. Holmes, J. D, Glennon.
Supercritical fluid generated stationary phases for liquid chromatography and capillary
electrochromatography // Anal. Chem., 2003, V. 75, P. 5860-5869.
31. L. Maldaner, I.C.S.F. Jardim. A new thermally immobilized fluorinated stationary
phase for RP-HPLC // J. Spec. Sci., 2010, V.33, P. 174-181.
32. L. Maldaner, I.C.S.F. Jardim. Preparation and characterization of a microwaveimmobilazed
fluorinated stationary phase for RP-LC // Chromatographia, 2010, V. 72, P.
617-626.
33. J. W. Shearer, L. Ding, S. V. Olesik. Solvation parameter models for retention on
perfluorinated and fluorinated low temperature glassy carbon stationary phases in reversedphase
liquid chromatography // Journal of Chromatography A, 2007, V. 1141, P. 73-80.
34. H. Itoh, T. Kinoshita, N. Nimura. High-performance liquid chromatographic
separation of nucleic acids on a fluorocarbon-bonded silica gel column // J. Chromatogr. A,
1994, V. 662, P. 95-99.
35. T. Kamiusuki, T. Monde, F. Nemoto, T. Konakahara, Y. Takahashi. Separation and
characterization of octylphenol ethoxylate surfactants used by reversed-phase highperformance
liquid chromatography on branched fluorinated silica gel columns // J.
Chromatogr. A, 1999, V. 852, P. 475-485.
36. F.M. Yamamoto, S. Rokushika. Retention properties of the fluorinated bonded phase
on liquid chromatography of aromatic hydrocarbons // J. Chromatogr. A, 2000, V. 898, P. 141-151.
37. S.Yang, M. G. Khaledi. Stationary phase effects on retention behavior of phenols in
micellar liquid chromatography: perfluorooctane vs. C18 // Analytica Chimica Acta, 1994,
V. 294, P. 135-143.
38. R. Dolfinger, D.C. Locke. Dependence of selectivity on eluent composition and
temperature in the HPLC separations of taxanes using fluorinated and hydrocarbon phases
// 2003, Anal. Chem., V. 75, P. 1355-1364.
39. W.G.H.M. Muijselaar, C.H.M.M. De Bruijn, F.M. Everaerts. Capillary zone
electrophoresis of proteins with a dynamic surfactant coating // J. Of Chromatogr., 1992, V.
605, P. 115-123.
40. A. Yurtsever, B. Saracoglu, A. Tuncel. CEC with new monolithic stationary phase
based on a fluorinated monomer, trifluoroethyl metacrylate // Electrophoresis, 2009, V.30,P. 589-598.
41. E. Sahlin, S. G. Weber. Capillary zone electrophoresis in laboratory-made fluorinated
ethylene propylene capillaries // Journal of Chromatography A, 2002, V. 972, №2, P. 283-287.
perfluoroalkyl carboxylate, sulfonate, and sulfonamide isomers by liquid chromatographytandem
mass spectrometry // Anal. Chem., 2007, V. 79, P. 6455-6464.
2. B. J. Stockman. 2-Fluoro-ATP as a Versatile Tool for 19F NMR-based Activity
Screening // J. Am. Chem. Soc., 2008, V. 130, P. 5870-5871.
3. Clark, L. C., Jr. Gollan. Survival of mammals breathing organic liquids equilibrated
with oxygen at a atmospheric pressure // F. Science, V. 152, P. 1966, 1755-1756.
4. S. Purser, P.M. Moore, S. Swallow, V. Gouverneur. Fluorine in medicinal chemistry //
Chem. Soc. Rev., 2008, V. 37, P. 320–330.
5. Riess J. G., Le Blanc M. Solubility and transport phenomena in perfluorochemicals
relevant to blood substitution and other biomedical applications // Pure Appl. Chem., 1982,
V. 54, P. 2383-2406.
6. K. Müller, C. Faeh, F. Diederich. Fluorine in pharmaceuticals: Looking beyond
intuition // Science 2007, V. 317, P. 1881-1886.
7. Horváth, I. T. Solvents from nature // Green Chem, 2008, V. 10, P. 1024–1028.
8. Brittain S.M., Ficarro S.B., Brock A., Peters E.C. Enrichment and analysis of peptide
subsets using fluorous affinity tags and mass spectrometry // Nat Biotechnol, 2005, V. 23,
P. 463-468.
9. Lehmler H.-J. Perfluorocarbon compounds as vehicles for pulmonary drug delivery //
Expert Opin Drug Deliv., 2007, V.4, P. 247-262.
10. D. O`Hagan, D. B. Harper. Fluorine-containing natural products // J. Fluorine Chem.,
1999, V. 100, P. 127–133.
11. I. De Miguel, A. Roueche, D. Betbeder. Separation of dipalmitoyl phosphatidyl
choline, cholesterol and their degradation products by high-performance liquid
chromatography on a perfluorinated stationary bonded phase // J. Chromatogr. A, 1999, V. 840, P. 31-38.
12. S. Yang, L.F. Resotoko Kruk, M.G. Khaledi. Fluorinated bonded stationary phases in
micellar liquid chromatography // Journal of Chromatography A, 1994, V. 664, P. 1-11.
13. N. Xiao, Y. B. Yu. Separation of fluorinated amino acids and oligopeptides from their
non-fluorinated counterparts using high-performance liquid chromatography // Journal of
Fluorine Chemistry, 2010, V. 13, P. 439-445.
14. S.L. Richeimer, M.C. Kent, M.W. Bernart. Reversed-phase high-performance liquid
chromatograpic method using a pentafluorophenyl bonded phase for analysis of
tocopherols // J. Chromatogr. A, 1994, V. 667, P. 75-80.
15. D.S. Bell, H.M. Cramer, A.D. Jones. Rational method development strategies on a
fluorinated liquid chromatography stationary phase: mobile phase ion concentration and
temperature effects on the separation of ephedrine alkaloids // Journal of Chromatography
A, 2005, V. 1095, P. 113-118.
16. K. Valko, S. Espinosa, C.M. Du, E. Bosch, M. Roses, C. Bevan, M.H. Abraham.
Unique selectivity of perfluorinated stationary phases with 2,2,2-trifluoroethanol as organic
mobile phase modifier // J. Chromatogr. A, 2001, V. 933, P. 73-81.
17. J. Flieger. Application of perfluorinated acids as ion-pairing reagents for reversedphase
chromatography and retention-hydrophobicity relationships studies of selected β-
blockers // J. Chromatogr. A, 2010, V. 1217, P. 540-549.
18. F. Vernona and G.T. Edwardsa. Gas-liquid chromatography on fluorinated stationary
phases: I. Hydrocarbons and fluorocarbons // Journal of Chromatography A, 1975, V. 110,
P. 73-80.
19. F. Vernona and G.T. Edwardsa. Gas-liquid chromatography on fluorinated stationary
phases: II. Fluorinated compounds containing a functional group // Journal of
Chromatography A, 1975, V. 114, P. 87-93.
20. R. M. Pomavillea, C. F. Poole. Thermally stable, highly fluorinated stationary phases
for gas chromatography // Analytica Chimica Acta, 1987, V. 200, P. 151-169.
21. H. Shinohara, N. Asakura, S. Tsujimora. Gas Chromatographic Characteristics of
Polytrifluoromonochloroethylene Columns as applied to Analysis of Uranium
Hexafluoride and other Volatile Inorganic Fluorides // Journal of nuclear science and Tech.,
1966, V. 3, P. 373-378.
22. A.G. Hamlin, G. Iveson, T.R. Phillips. Analysis of volatile inorganic fluorides by gasliquid
chromatography // Anal. Chem. 1963, № 56, P. 2037-2040.
23. Т. М. Рощина, С. В. Глазкова, А. Д. Хрычева. Газохроматографическое
исследование свойств поверхности фторированного углерода // Вестн. Моск. Ун-та.
Серия 2. Химия, 2005, Т. 46, №1, С. 29-33.
24. Т. М. Рощина, С. В. Глазкова, А. Д. Хрычева, В.Г. Макотченко, М. Л. Пантюхин.
Исследование влияния фторрования на свойства поверхности углеродных
материаловметодом газовой хроматографии // Вестн. Моск. Ун-та. Серия 2. Химия,
2007, Т. 48, №2, С. 80-85.
25. T.M. Reed Ill. Gas-Liquid Partition Chromatography of Fluorocarbons // Anal.
Chem., 1958, V. 30, P. 221-228.
26. А.Н. Король, В.М. Сахаров. К вопросу избирательности фторсодержащих
неподвижных фаз в газовой хроматографии // Газовая хроматография, 1967, вып. 7,
С. 39-47.
27. В.В. Бражников, Л.И. Мосева, К.И. Сакодынский, В.А. Сокольский.
Модифицированный фторопластовый носитель // Газовая хроматография, 1969, вып.
8, С. 80-85.
28. H. Glatz, C. Blay, H. Engelhardt, W. Bannwarth. New fluorous reversed phase silica
gels for HPLC separations of perfluorinated compounds // Chromatographia, 2004, 59, № 9/10, P. 567-570.
29. M. P. Krafft, Fr. Jeannaux, M. Le Blanc, J. G. Riess, A. Berthod. Highly fluorinated
stationary phases for analysis of polyfluorinated solutes by reversed-phase highperformance
liquid chromatography // Anal. Chem., 1988, 60 (18), P. 1969–1972.
30. L. O. Healy, V. P. Owens, T. O`Mahony, S. Srijaranai, J. D. Holmes, J. D, Glennon.
Supercritical fluid generated stationary phases for liquid chromatography and capillary
electrochromatography // Anal. Chem., 2003, V. 75, P. 5860-5869.
31. L. Maldaner, I.C.S.F. Jardim. A new thermally immobilized fluorinated stationary
phase for RP-HPLC // J. Spec. Sci., 2010, V.33, P. 174-181.
32. L. Maldaner, I.C.S.F. Jardim. Preparation and characterization of a microwaveimmobilazed
fluorinated stationary phase for RP-LC // Chromatographia, 2010, V. 72, P.
617-626.
33. J. W. Shearer, L. Ding, S. V. Olesik. Solvation parameter models for retention on
perfluorinated and fluorinated low temperature glassy carbon stationary phases in reversedphase
liquid chromatography // Journal of Chromatography A, 2007, V. 1141, P. 73-80.
34. H. Itoh, T. Kinoshita, N. Nimura. High-performance liquid chromatographic
separation of nucleic acids on a fluorocarbon-bonded silica gel column // J. Chromatogr. A,
1994, V. 662, P. 95-99.
35. T. Kamiusuki, T. Monde, F. Nemoto, T. Konakahara, Y. Takahashi. Separation and
characterization of octylphenol ethoxylate surfactants used by reversed-phase highperformance
liquid chromatography on branched fluorinated silica gel columns // J.
Chromatogr. A, 1999, V. 852, P. 475-485.
36. F.M. Yamamoto, S. Rokushika. Retention properties of the fluorinated bonded phase
on liquid chromatography of aromatic hydrocarbons // J. Chromatogr. A, 2000, V. 898, P. 141-151.
37. S.Yang, M. G. Khaledi. Stationary phase effects on retention behavior of phenols in
micellar liquid chromatography: perfluorooctane vs. C18 // Analytica Chimica Acta, 1994,
V. 294, P. 135-143.
38. R. Dolfinger, D.C. Locke. Dependence of selectivity on eluent composition and
temperature in the HPLC separations of taxanes using fluorinated and hydrocarbon phases
// 2003, Anal. Chem., V. 75, P. 1355-1364.
39. W.G.H.M. Muijselaar, C.H.M.M. De Bruijn, F.M. Everaerts. Capillary zone
electrophoresis of proteins with a dynamic surfactant coating // J. Of Chromatogr., 1992, V.
605, P. 115-123.
40. A. Yurtsever, B. Saracoglu, A. Tuncel. CEC with new monolithic stationary phase
based on a fluorinated monomer, trifluoroethyl metacrylate // Electrophoresis, 2009, V.30,P. 589-598.
41. E. Sahlin, S. G. Weber. Capillary zone electrophoresis in laboratory-made fluorinated
ethylene propylene capillaries // Journal of Chromatography A, 2002, V. 972, №2, P. 283-287.
Published
2019-11-25
How to Cite
Nayden, S. V., & Kartsova, L. A. (2019). Organic fluoro-containing compounds as chromatographic and elecrophoretic systems components. Sorbtsionnye I Khromatograficheskie Protsessy, 12(4). Retrieved from https://journals.vsu.ru/sorpchrom/article/view/1835
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