Enantiomeric separation of chiral ruthenium(II) complexes using capillary electrophoresis

Chirality

Volumn 21, Issue 1, 2009, Pages 208-217

  Jiang, Chunxia ^a   Tong, Man Yung ^a   Amstrong, Daniel W ^a   Perera, Sirantha ^a   Bao, Ye ^a   MacDonnell, Frederick M ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

Chiral capillary electrophoresis; Complexes; Cyclodextrin; Enanlioseparation; Micellar capillary electrophoresis; Micelle sodium dodecylsulfate; Transition metal complexes; Tris(diimine)ruthenium(II)

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; BETA CYCLODEXTRIN; BUFFER; CYCLODEXTRIN; GAMMA CYCLODEXTRIN DERIVATIVE; RUTHENIUM COMPLEX; DODECYL SULFATE SODIUM; ORGANOMETALLIC COMPOUND; RUTHENIUM;

ARTICLE; CAPILLARY ELECTROPHORESIS; CAPILLARY ZONE ELECTROPHORESIS; CHEMICAL STRUCTURE; CHIRALITY; CONCENTRATION RESPONSE; DERIVATIZATION; ENANTIOMER; MICELLAR CAPILLARY ELECTROPHORESIS; PH; PRIORITY JOURNAL; STEREOISOMERISM; CHEMISTRY; ISOLATION AND PURIFICATION; MICELLE;

BUFFERS; CYCLODEXTRINS; ELECTROPHORESIS, CAPILLARY; HYDROGEN-ION CONCENTRATION; MICELLES; ORGANOMETALLIC COMPOUNDS; RUTHENIUM; SODIUM DODECYL SULFATE; STEREOISOMERISM;

EID: 59849088238     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20641     Document Type: Article

References (74)

1. Patterson BT, Foley FM, Richards D, Keene FR. Synthetic and stereo-chemical studies of dinuclear ruthenium complexes with mixed terminal ligands. J Chem Soc Dalton Trans 2003;4:709-714.
2. Eustache F, Dalko PI, Cossy J. Enantioselective Monoreduction of 2-alkyl-1,2-diketones mediated by chiral ruthenium catalysts. Dynamic Kinetic Resolution. Org Lett 2002;4:1263-1265.
3. Yamagishi A. Optical resolution and asymmetric syntheses. Chem Austr 1987;54:278.
4. Fujita S, Sato H, Kakegawa N, Yamagishi A. Enantioselective photooxidation of a sulfide by a chiral ruthenium(II) complex immobilized on a montmorillonite clay surface: the role of weak interactions in asymmetric induction. J Phys Chem B 2006;110:2533-2540.
5. Hartshorn RM, Barton JK. Novel dipyridophenazine complexes of ruthenium(II): exploring luminescent reporters of DNA. J Am Chem Soc 1992;114:5919-5925.
6. Hoshino N, Matsuoka Y, Okamoto K, Yamagishi A. Δ-[Ru(acac)2L] (L = a Mesogenic Derivative of bpy) as a novel chiral dopant for nematic liquid crystals with large helical twisting power. J Am Chem Soc 2003;125:1718-1719.
7. Szmacinski H, Terpetschnig E, Lakowicz JR. Synthesis and evaluation of Ru-complexes as anisotropy probes for protein hydrodynamics and immunoassays of high-molecular-weight antigens. Biophys Chem 1996;62:109-120.
8. Guo X, Castellano FN, Li L, Lakowicz JR. A long-lifetime Ru(II) metal-ligand complex as a membrane probe. Biophys Chem 1998;71:51-62.
9. Szmacinski H, Castellano FN, Terpetschnig E, Dattelbaum JD, Lakowicz JR, Meyer GJ. Long-lifetime Ru(II) complexes for the measurement of high molecular weight protein hydrodynamics. Biochimica et Biophysica Acta 1998;1383:151-159.
10. Li L, Szmacinski H, Lakowicz JR. Long-lifetime lipid probe containing a luminescent metal-ligand complex. Biospectroscopy 1997;3:155-159.
11. Barton JK. Metals and DNA: molecular left-handed complements. Science 1986;233:727-734.
12. Pieper T, Keppler BK. Tumor-inhibiting ruthenium complexes - formulation and analytical characterization. Analusis 1998;26:M84-M87.
13. Yuan D, Pietrzyk DJ. Separation and indirect detection of small-chain peptides using chromophoric mobile phase additives. J Chromatogr 1990;509:357-368.
14. Yamagishi A, Ohnishi R. Clay column chromatography for optical resolution: partial resolution of tris(acetylacetonato)metal(III) on a Λ-tris(1,10-phenanthroline)ruthenium(II) montmorillonite column. J Chromatogr 1982;245:213-218.
15. 2+ laponite columns towards 1,1′-binaphthol. Appl Clay Sci 1996;11:1-10.
16. Yamagishi A. Application of clay to optical resolution. Seramikkusu 1989;24:1048-1053.
17. Yamagishi A, Makino H, Nakamura Y, Sato H. Separation of isomers of cobalt(III) complexes by liquid chromatography on a column packed with a clay-ruthenium(II) complex adduct. Clays Clay Minerals 1992;40:359-361.
18. Burstall FH. Optical activity dependent on co-ordinated bivalent ruthenium. J Chem Soc 1936;173-175
19. Goss CA, Abruña HD. Spectral, electrodiemical and eleclrocatalytic properties of 1,10-phenanthroline-5,6-dione complexes of transition metals. Inorg Chem 1985;24:4263-4267.
20. Konduri R. Novel ruthenium(II) polypyridyl supramolecules capable of storing multiple electrons upon photoirrediation. Ph.D. thesis, University of Texas at Arlington, TX; 2003.
21. Bosnich B, Dwyer FF. Bis-1,10-phenanthroline complexes of divalent ruthenium. Aust J Chem 1966;19:2229-2233.
22. Broomhead JA, Young CG, Hood P. Tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate. Inorg Synth 1982;21:127-128.
23. Kim M-J, Konduri R, Ye H, MacDonnell FM, Puntoriero F, Serroni S, Campagna S, Holder T, Kinsel G, Rajeshwar H. Dinuclear ruthenium(II) polypyridyl complexes containing large, redox-active, aromatic bridging ligands: synthesis, characterization, and intramolecular quenching of MLCT excited states. Inorg Chem 2002;41:2471-2476.
24. 2+ species (pp = Bidentate polypyridyl ligand) and their use in the stereoselective synthesis of ligand-bridge dinuclear complexes. Inorg Chem 1995;34:3857-3858.
25. Hua X, von Zelewsky A. Enantiomerically pure chiral RuII(L,L)2 building blocks for coordination compounds. Inorgan Chem 1995;34:5791-5797.
26. 2]n+ species (n = 0, 2; X = CN-, Cl-, py). Inorg Chim Acta 1996;249:5-7.
27. 2+. J Am Chem Soc 1993; 115:3448-3454.
28. 2+ by anionic cyclodextrins. Chem Lett 2000;6:698-699.
29. 2+ studied with linear and circular dichroism. J Am Chem Soc 1990;112:1971-1982.
30. Herbert BJ, Carpenter HE, Kane-Maguire NAP, Wheeler JF, Use of chiral capillary electrophoresis and circular dichroism for the determination of absolute values of Δ.vepsiln. for diimine transition metal complexes. Anal Chim Acta 2004;514:27-35.
31. Rutherford TJ, Pellegrini PA, Aldrich-Wright J, Junk PC, Keene FR. Isolation of enantiomers of a range of tris(bidentate)ruthenium(II) species using chromatographic resolution and stereoretentive synthetic methods. Eur J Inorg Chem 1998;1167-1188.
32. Keene FR. Isolation and characterization of stereoisomers in di- and tri-nuclear complexes. Chem Soc Rev 1998;7:185-193.
33. Fletcher NC, Junk PC, Reitsma DA, Keene FR. Chromatographic separation of stereoisomers of ligand-bridged diruthenium polypyridyl species. J Chem Soc Dalton Trans 1998;1:133-138.
34. Yoshikawa Y, Yamasaki K. Chromatographic resolution of metal complexes on Sephadex ion exchangers. Coord Chem Rev 1979;28:205-229.
35. Aldrich-Wright J, Vagg RS, Williams PA. HPLC separation of diastereomeric metal complexes of the form Δ,Λ-[Ru(diimine)2(S)-aminoacidate]. Aust J Chem 2003; 56:1193-1200.
36. Fletcher NC, Keene FR. Anion interactions with (polypyridyl)ruthenium complexes, their importance in the cation-exchange chromatographic separation of stereoisomers of dinuclear species. J Chem Soc Dalton Trans 1999;17:683-689.
37. Dmochowski IJ, Winkler JR, Gray HB. Enantiomeric discrimination of Ru-substrates by cytochrome P450cam. J Inorg Biochem 2000;81:221-228.
38. Aoki F, Hesek D, Ishida H, Inoue Y. Chromatographic chiral separation of ruthenium tris(bipyridine) complexes. Chromatography 2000; 21:133-134.
39. Aldrich-Wright J, Greguric I, Vagg RS, Vickery K, Williams PA. Development of DNA-immobilized chromatographic stationary phases for optical resolution and DNA-affinity comparison of metal complexes. J Chromatogr A 1995;718:436-443.
40. 2+ on a DNA-hydroxylapatite column. J Am Chem Soc 1991;113:1141-1142.
41. Smith JA, Keene FR. Separation of stereoisomers of dinuclear metal complexes by binding affinity chromatography using non-duplex DNA. Chem Commun 2006;2583-2585.
42. Browne WR, O'Connor CM, Villani C, Vos JG. Separation and photophysical properties of the ΔΔ, ΛΛ, and ΛΛ stereoisomers of a dinuclear ruthenium(II) Complex. Inorg Chem 2001; 40:5461-5464.
43. Gasparrini F, D'Acquarica I, Vos JG, O'Connor CM, Villani C. Efficient enantiorecognition of ruthenium(II) complexes by silica-bound teicoplanin. Tetrahedron: Asymmetry 2000;11:3535-3541.
44. Wan H, Blomberg LG. Chiral separation of amino acids and peptides by capillary electrophoresis. J Chromatogra A 2000;875:43-38.
45. Sánchez-Hernández L, Crego AL, Marina ML, García-Ruiz C. Sensitive chiral analysis by CE: an update. Electrophoresis 2008;29:237-251.
46. Chankvetadze B. Enantioseparations by using capillary electrophoretic techniques. The story of 20 a few more years. J Chromatogra A 2007;1168:45-70.
47. Ali I, Kumerer K, Aboul-Enein HY. Mechanistic principles in chiral separations using liquid chromatography. Chromatographia 2006;63: 295-307.
48. Lin C, Li Y, Chen S. Recent progess in pharmacokinetic applications of capillary electrophoresis. Electrophoresis 2003;24:4106-4115.
49. Evans CE, Stalcup AM. Comprehesive strategy for chiral separations using sulfated cyclodextrins in capillary electrophoresis. Chirality 2003;15:709-723.
50. Zhang J, Konecny J, Glatz Z, Hoogmartens J, Van Schepdael A. Application of capillary electrophoresis in drug metabolism studies. Curr Anal Chem 2007;3:197-217.
51. Altria KD, Chen AB. Clohs L. Capillary electrophoresis as a routine analytical tool in pharmaceutical analysis. LC-GC Europe 2001;14:740-744.
52. Ahmad A. Recent Developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis. Electrophoresis 2001;22:3107-3130.
53. Haginaka J. Enantiomer separation of drugs by capillary electrophoresis using proteins as chiral selectors. J Chromatogr A 2000;87:235-254.
54. Rodriguez MA, Liu Y, McCulla R, Jenks WS, Armstrong DW. Enantio-separation of chiral sulfoxides and sulfinate esters by capillary electrophoresis. Electrophoresis 2002;23:1561-1570.
55. Jiang C, Armstrong DW, Lantz AW, Péter A, Tóth G. Enantiomeric separation of synthetic amino acids using capillary zone electrophoresis. J Liq Chromatogra Rel Tech 2007;30:1421-1436.
56. Holder E, Schoetz G, Schurig V, Lindner E. Synthesis and enantiomer separation of a modified tris(2,2′-bipyridine)ruthenium(II) complex. Tetrahedron: Asymmetry 2001;12:2289-2293.
57. Holder E, Trapp O, Trapp G, Marin V, Hoogenboom R, Schubert US. Synthesis, complete characterization, and enantioselective electrokinetic separation of functionalized ruthenium complex enantiomers. Chirality 2004;16:363-368.
58. Holder E, Trapp G, Grimm JC, Schurig V, Lindner E. Synthesis and rapid enantiomeric separation of the chiral mixed ligand [5-(4-hydroxybutyl]-5′-methyl-2,2′-bipyridine]- bis(1,10-phenanthroline)-ruthenium(II) complex by electrokinetic chromatography. Tetrahedron: Asymmetry 2002;13:2673-2678.
59. Shelton CM, Seaver KE, Wheeler JF, Kane-Maguire NAP. Application of capillary electrophoresis for the assessment of enantiometic purity of α-diimine transition metal complexes. Inorg Chem 1997;36:1532-1533.
60. Elshihabi S, Black KD, Sutton J K, Woody KA, Burke JA Jr, Bushey MM. Micellar electrokinetic chromatography of tri aza aromatic ligand compounds of iron (II): influence of bile salt type on enantiomeric separation. Electrophoresis 2001;22:3771-3777.
61. Chankvetadze B, Endresz G, Blaschke K. About some aspects of the use of charged cyclodextrins for capillary electrophoresis enantioseparation, Electrophoresis 1994;15:804-807.
62. See MM, Elshihabi S, Burke JA Jr, Bushey MM. Resolution effects of organic additives on the MEKC enantiomeric separations of Tri Aza aromatic ligand compounds of iron(II). J Microcol Sep 1995;7:199-206.
63. Harris JE, Desai N, Seaver KE, Watson RT. Chiral separations of transition metal complexes using capillary zone electrophoresis. J Chromatogra A 2001;919:427-436.
64. Fanali S, Ossicini L, Foret F, Bocek P. Resolution of optical isomers by capillary zone electrophoresis: study of enantiomeric and distereoisomeric cobalt(III) complexes with ethylenediamine and amino acid ligands. J Microcol Sep 1989;1:190-194.
65. Grossman PD, Colburn JC. Capillary electrophoresis, theory and practice. New York: Academic Press; 1992.
66. Fanali S. Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors. J Chromatogra A 2000;875:89-122.
67. Fanali S. Separation of optical isomers by capillary zone electrophoresis based on host-guest complexation with cyclodextrins. J Chroatogr A 1989;474:441-446.
68. Rizzi A. Fundamental aspects of chiral separations by capillary electrophoresis. Electrophoresis 2001;22:3079-3016.
69. Lantz AW, Rozhkov RV, Larock RC, Armstrong DW. Enantiomeric separation of neutral hydrophobic dihydrofuroflavones by cyclodextrin-modified micellar capillary electrophoresis. Eletrophoresis 2004;25:2727-2734.
70. Jiang C, Armstrong DW, Péter A, Fülöp F. Enantiomeric separation of a series of β-lactams using capillary zone electrophoresis. J Liq Chromatogra Rel Tech 2007;30:1709-1721.
71. Egger MD, Liu Y, Sevcík J, Etsarová E, Rozhkov R, Larock RC, Armstrong DW. Enantioseparaiion of dihydrofurocoumarin derivatives by various separation modes of capillary electrophoresis. Electrophoresis 2003;24:2650-2656.
72. Pak C, Marriott PJ, Carpenter PD, Amiet RG. Enantiomeric separation of propranolol and selected metabolites by using capillary electrophoresis with hydroxypropyl-cyclodextrin as chiral selector. J Chromatogra A 1998;793:357-364.
73. Altria KD, Goodall DM, Rogan MM. Chiral separation of β-amino alcohols by capillary electrophoresis using cyclodextrins as buffer additives. I. Effect of varying operating parameters. Chromatographia 1992;34:19-24.
74. Guttman A, Paulus A, Cohen AS, Geinberg N, Karger BL. Use of complexing agents for selective separation in high-performance capillary electrophoresis Chiral resolution via cyclodextrins incorporated within polyacrylamide gel column. J Chromatogr 1998;448:41-53.