Enantioseparation of dansyl amino acids by HPLC on a monolithic column dynamically coated with a vancomycin derivative

Biomedical Chromatography

Volumn 24, Issue 11, 2010, Pages 1213-1219

  Pittler, Elfriede ^a   Schmid, Martin G ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

Dansyl amino acids; Dynamic coating; Enantiomer separation; Macrocyclic antibiotic; Monolithic column

Indexed keywords

AMINO ACIDS; COATINGS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

CHIRAL SELECTOR; CHIRAL STATIONARY PHASE; DANSYL AMINO ACIDS; DYNAMIC COATING; ENANTIOMERS SEPARATION; ENANTIOSEPARATIONS; MACROCYCLIC ANTIBIOTICS; MONOLITHIC COLUMNS; MONOLITHICS; VANCOMYCIN;

ENANTIOMERS;

ALKYL GROUP; AMINO ACID; DANSYL CHLORIDE; VANCOMYCIN DERIVATIVE;

ARTICLE; CHIRALITY; ELUTION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; REPRODUCIBILITY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SEPARATION TECHNIQUE;

EID: 77958507445     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1430     Document Type: Article

References (63)

1. Aboul-Enein HY and Hefnawy MM. Chiral analysis of butaclamol enantiomers in human plasma by HPLC using a macrocyclic antibiotic (vancomycin) chiral stationary phase and solid phase extraction. Chirality 2004; 16(3): 147-152.
2. Altmaier S and Cabrera K. Structure and performance of silica-based monolithic HPLC columns. Journal of Separation Science 2008; 31(14): 2551-2559.
3. Armstrong DW and Zhou Y. Use of a macrocyclic antibiotic as the chiral selector for enantiomeric separations by TLC. Journal of Liquid Chromatrography & Related Technologies 1994; 17(8): 1651-1707.
4. Armstrong DW, Rundlett KL and Chen JR. Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis. Chirality 1994a; 6(6): 496-509.
5. Armstrong DW, Tang Y, Chen S, Zhou Y, Bagwill C and Chen J. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Analytical Chemistry 1994b; 66: 1473-1484.
6. Bayer M, Hansel C and Mosandl A. Enantiomer separation on monolithic silica HPLC columns using chemically bonded methylated and methylated/acetylated 6-O-tert-butyldimethylsilylated beta-cyclodextrin. Journal of Separation Science 2006; 29(11): 1561-1570.
7. Bell CJ, Hood SD and Nutt DJ. Acute tryptophan depletion. Part II: clinical effects and implications. The Australian and New Zealand Journal of Psychiatry 2005; 39(7): 565-574.
8. Berthod A, Liu Y, Bagwill C and Armstrong DW. Facile liquid chromatographic enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase. Journal of Chromatography A 1996; 731(1-2): 123-137.
9. Bhushan R and Gupta D. Thin-layer chromatography separation of enantiomers of verapamil using macrocyclic antibiotic as a chiral selector. Biomedical Chromatography 2005; 19(6): 474-478.
10. Boatto G, Nieddu M, Faedda MV and de Caprariis P. Enantiomeric separation by HPLC of 1, 4-dihydropyridines with vancomycin as chiral selector. Chirality 2003; 15(6): 494-497.
11. Bosakova Z, Curinova E and Tesarova E. Comparison of vancomycin-based stationary phases with different chiral selector coverage for enantioselective separation of selected drugs in high-performance liquid chromatography. Journal of Chromatography A 2005; 1088(1-2): 94-103.
12. Cabrera K. Applications of silica-based monolithic HPLC columns. Journal of Separation Science 2004; 27(10-11): 843-852.
13. Chankvetadze B, Ikai T, Yamamoto C and Okamoto Y. High-performance liquid chromatographic enantioseparations on monolithic silica columns containing a covalently attached 3, 5-dimethylphenylcarbamate derivative of cellulose. Journal of Chromatography A 2004a; 1042(1-2): 55-60.
14. Chankvetadze B, Yamamoto C, Tanaka N, Nakanishi K and Okamoto Y. High-performance liquid chromatographic enantioseparations on capillary columns containing monolithic silica modified with cellulose tris(3, 5-dimethylphenylcarbamate). Journal of Separation Science 2004b; 27(10-11): 905-911.
15. Chankvetadze B, Kubota T, Ikai T, Yamamoto C, Kamigaito M, Tanaka N, Nakanishi K and Okamoto Y. High-performance liquid chromatographic enantioseparations on capillary columns containing crosslinked polysaccharide phenylcarbamate derivatives attached to monolithic silica. Journal of Separation Science 2006a; 29(13): 1988-1995.
16. Chankvetadze B, Yamamoto C, Kamigaito M, Tanaka N, Nakanishi K and Okamoto Y. High-performance liquid chromatographic enantioseparations on capillary columns containing monolithic silica modified with amylose tris(3, 5-dimethylphenylcarbamate). Journal of Chromatography A 2006b; 1110(1-2): 46-52.
17. Chen Z, Zeng S and Yao T. Separation of beta-receptor blockers and analogs by capillary liquid chromatography (CLC) and pressurized capillary electrochromatography (pCEC) using a vancomycin chiral stationary phase column. Pharmazie 2007; 62(8): 585-592.
18. Davankov VA, Bochkov AS, Kurganov AA, Roumeliotis P and Unger KK. Ligand-exchange chromatography of racemates XIII. A study on the separation of unmodified α-amino acid racemates by reversed phase high performance liquid chromatography. Chromatographia 1980; 13: 677-685.
19. Dermaux A, Lynen F and Sandra P. Chiral capillary electrochromatography on a vancomycin stationary phase. Journal of High Resolution Chromatography 1998; 21(10): 575-576.
20. Desiderio C, Aturki Z and Fanali S. Use of vancomycin silica stationary phase in packed capillary electrochromatography I. Enantiomer separation of basic compounds. Electrophoresis 2001; 22(3): 535-543.
21. Dong X, Dong J, Ou J, Zhu Y and Zou H. Preparation and evaluation of a vancomycin-immobilized silica monolith as chiral stationary phase for CEC. Electrophoresis 2007; 28(15): 2606-2612.
22. D'Orazio G, Aturki Z, Cristalli M, Quaglia MG and Fanali S. Use of vancomycin chiral stationary phase for the enantiomeric resolution of basic and acidic compounds by nano-liquid chromatography. Journal of Chromatography A 2005; 1081(1): 105-113.
23. Fanali S, Catarcini P and Quaglia MG. Use of vancomycin silica stationary phase in packed capillary electrochromatography: III. Enantiomericseparation of basic compounds with the polar organic mobile phase. Electrophoresis 2002; 23(3): 477-485.
24. Gübitz G, Jellenz W and Santi W. Separation of the optical isomers of amino acids by ligand-exchange chromatography using chemically bonded chiral phases. Journal of Chromatography 1981; 203: 377-384.
25. Guillaume YC and Andre C. A novel chiral column for the HPLC separation of a series of dansyl amino and arylalkanoic acids. Talanta 2008; 76(5): 1261-1264.
26. Guiochon G. Monolithic columns in high-performance liquid chromatography. Journal of Chromatography A 2007; 1168(1-2): 101-168.
27. Haroun M, Ravelet C, Grosset C, Ravel A, Villet A and Peyrin E. Reversal of the enantiomeric elution order of some aromatic amino acids using reversed-phase chromatographic supports coated with the teicoplanin chiral selector. Talanta 2006; 68(3): 1032-1036.
28. Hefnawy MM, Sultan MA and Al-Shehri MM. HPLC separation technique for analysis of bufuralol enantiomers in plasma and pharmaceutical formulations using a vancomycin chiral stationary phase and UV detection. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2007; 856(1-2): 328-336.
29. Hong W and Blomberg LG. Enantiomeric separation by capillary electrophoresis of di- and tri-peptides derivatized with 9-fluorenylmethyl chloroformate using vancomycin as chiral selector. Journal of Microcolumn Separations 1996; 8(5): 339-344.
30. Ilisz I, Berkecz R and Peter A. HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic-based chiral stationary phases: a review. Journal of Separation Science 2006; 29(10): 1305-1321.
31. Ilisz I, Berkecz R and Peter A. Retention mechanism of high-performance liquid chromatographic enantioseparation on macrocyclic glycopeptide-based chiral stationary phases. Journal of Chromatography A 2008; 1216(10): 1845-1860.
32. Ishizuka N, Minakuchi HKN, Soga N, Nagayama H, Hosoya K and Tanaka N. Performance of a monolithic silica column in a capillary under pressure-driven and electrodriven conditions. Analytical Chemistry 2000; 72: 1275-1280.
33. Kafkova B, Bosakova Z, Tesarova E, Coufal P, Messina A and Sinibaldi M. Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography. Chirality 2006; 18(7): 531-538.
34. Kang J, Wistuba D and Schurig V. Fast enantiomeric separation with vancomycin as chiral additive by co-electroosmotic flow capillary electrophoresis: increase of the detection sensitivity by the partial filling technique. Electrophoresis 2003; 24(15): 2674-2679.
35. Kang J, Bischoff D, Jiang Z, Bister B, Sussmuth RD and Schurig V. A mechanistic study of enantiomeric separation with vancomycin and balhimycin as chiral selectors by capillary electrophoresis. Dimerization and enantioselectivity. Analytical Chemistry 2004; 76(8): 2387-2392.
36. Karlsson C, Karlsson L, Armstrong DW and Owens PK. Evaluation of a vancomycin chiral stationary phase in capillary electrochromatography using polar organic and reversed-phase modes. Analytical Chemistry 2000; 72(18): 4394-4401.
37. Kornysova O, Owens PK and Maruska A. Continuous beds with vancomycin as chiral stationary phase for capillary electrochromatography. Electrophoresis 2001; 22(15): 3335-3338.
38. Lubda D, Cabrera K, Nakanishi K and Lindner W. Monolithic silica columns with chemically bonded beta-cyclodextrin as a stationary phase for enantiomer separations of chiral pharmaceuticals. Analytical and Bioanalytical Chemistry 2003; 377(5): 892-901.
39. Lubda D and Lindner W. Monolithic silica columns with chemically bonded tert-butylcarbamoylquinine chiral anion-exchanger selector as a stationary phase for enantiomer separations. Journal of Chromatography A 2004; 1036(2): 135-143.
40. Nadalini G, Dondi F, Massi A, Dondoni A, Zhang T and Cavazzini A. High-performance liquid chromatographic separation of dihydropyrimidine racemates on polysaccharide-derived chiral stationary phases. Journal of Chromatography A 2006; 1126(1-2): 357-364.
41. Natalini B, Sardella R, Macchiarulo A and Pellicciari R. Dynamic ligand-exchange chiral stationary phase from S-benzyl-(R)-cysteine. Chirality 2006; 18(7): 509-518.
42. Natalini B, Sardella R, Macchiarulo A and Pellicciari R. S-trityl-(R)-cysteine, a powerful chiral selector for the analytical and preparative ligand-exchange chromatography of amino acids. Journal of Separation Science 2008; 31(4): 696-704.
43. Nunez O, Nakanishi K and Tanaka N. Preparation of monolithic silica columns for high-performance liquid chromatography. Journal of Chromatography A 2008; 1191(1-2): 231-252.
44. Pehourcq F, Jarry C and Bannwarth B. Chiral resolution of flurbiprofen and ketoprofen enantiomers by HPLC on a glycopeptide-type column chiral stationary phase. Biomedical Chromatography 2001; 15(3): 217-222.
45. Remelli M, Fornasari P and Pulidori F. Study of retention, efficiency and selectivity in chiral ligand-exchange chromatography with a dynamically coated stationary phase. Journal of Chromatography A 1997; 761: 79-89.
46. Schmid MG, Schreiner K, Reisinger D and Gübitz G. Fast chiral separation by ligand-exchange HPLC using a dynamically coated monolithic column. Journal of Separation Science 2006; 29(10): 1470-1475.
47. Sharp VS, Letts MN, Risley DS and Rose JP. Enantiomeric separation of dansyl amino acids using macrocyclic antibiotics as chiral mobile phase additives by narrow-bore high-performance liquid chromatography. Chirality 2004; 16(3): 153-161.
48. Sun Q and Olesik SV. Chiral separation by simultaneous use of vancomycin as stationary phase chiral selector and chiral mobile phase additive. Journal of Chromatography B: Biomedical Sciences and Applications 2000; 745(1): 159-166.
49. Tanaka N, Kobayashi H, Ishizuka N, Minakuchi HKN, Hosoya K and Ikegami T. Monolithic silica columns for high-effiency chromatographic separations. Journal of Chromatography A 2002; 965: 35-49.
50. Vespalec R, Billiet HA, Frank J and Bocek P. Vancomycin as a chiral selector in capillary electrophoresis: an appraisal of advantages and limitations. Electrophoresis 1996; 17(7): 1214-1221.
51. Wan H and Blomberg LG. Enantioseparation of amino acids and dipeptides using vancomycin as chiral selector in capillary electrophoresis. Electrophoresis 1996; 17(12): 1938-1944.
52. Wang P, Liu D, Jiang S, Xu Y, Gu X and Zhou Z. The chiral resolution of pesticides on amylose-tris(3, 5-dimethylphenylcarbamate) CSP by HPLC and the enantiomeric identification by circular dichroism. Chirality 2008; 20(1): 40-46.
53. Wang Z, Wang J, Hu Z and 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; 28(6): 938-943.
54. Ward TJ and Farris AB 3rd. Chiral separations using the macrocyclic antibiotics: a review. Journal of Chromatography A 2001; 906(1-2): 73-89.
55. Ward TJ and Rabai CM. Chiral separations using the macrocyclic antibiotics in capillary electrophoresis. Methods in Molecular Biology 2004; 243: 255-263.
56. Wikstrom H, Svensson LA, Torstensson A and Owens PK. Immobilisation and evaluation of a vancomycin chiral stationary phase for capillary electrochromatography. Journal of Chromatography A 2000; 869(1-2): 395-409.
57. Wurtmann RJ. Genes, stress and depression. Metabolism 2005; 54: 16-19.
58. Xiao LT, Zhang B, Lee JT, Hui F and Armstrong DW. Reversal of enantiomeric elution order on macrocyclic glycopeptide chiral stationary phases. Journal of Liquid Chromatography & Related Technologies 2001; 24(17): 2673-2684.
59. Xiao TL and Armstrong DW. Enantiomeric separations by HPLC using macrocyclic glycopeptide-based chiral stationary phases: an overview. Methods in Molecular Biology 2004; 243: 113-171.
60. Yamamoto C, Fujisawa M, Kamigaito M and Okamoto Y. Enantioseparation using urea- and imide-bearing chitosan phenylcarbamate derivatives as chiral stationary phases for high-performance liquid chromatography. Chirality 2008; 20(3-4): 288-294.
61. Yao C, Tang S, Gao R, Jiang C and Yan C. Enantiomer separations on a vancomycin stationary phase and retention mechanism of pressurized capillary electrochromatography. Journal of Separation Science 2004; 27(13): 1109-1114.
62. Zaher M, Baussanne I, Ravelet C, Halder S, Haroun M, Fize J, Decout JL and Peyrin E. Copper(II) complexes of lipophilic aminoglycoside derivatives for the amino acid enantiomeric separation by ligand-exchange liquid chromatography. Journal of Chromatography A 2008; 1185(2): 291-295.
63. Zhang D, Xu X and Ma S. The study of enantioseparation of zolmitriptan on vancomycin-bonded chiral stationary phase. Journal of Separation Science 2005; 28(18): 2501-2504.