Enantiomeric separation of isochromene derivatives by cyclodextrin-modified micellar capillary electrophoresis

Journal of Liquid Chromatography and Related Technologies

Volumn 31, Issue 14, 2008, Pages 2035-2052

  Bao, Ye ^a   Yue, Dawei ^b   Cà, Nicola Della ^b   Larock, Richard C ^b   Armstrong, Daniel W ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

^b IOWA STATE UNIVERSITY   (United States)

Author keywords

Capillary electrophoresis; Chiral separation; Cyclodextrin; Isochromene derivatives; Micelle

Indexed keywords

ALKALI METALS; CAPILLARY ELECTROPHORESIS; ELECTROCHEMISTRY; ELECTROOSMOSIS; ELECTROPHORESIS; ISOMERS; OPTIMIZATION; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; SODIUM; SODIUM SULFATE; SULFATE MINERALS;

ACIDIC PH; ANALYTE; ANALYTES; CHIRAL SELECTORS; CYCLODEXTRIN (CYDS); ELECTRO OSMOTIC (EO) FLOWS; ENANTIO-SEPARATION; ENANTIOMERIC SEPARATIONS; IN ORDER; ORGANIC MODIFIERS; REVERSE POLARITY; SEPARATION CONDITIONS; SEPARATION EFFICIENCY; SODIUM DODECYL SULFATE (SDS);

SEPARATION;

CHROMENE DERIVATIVE; DODECYL SULFATE SODIUM; GAMMA CYCLODEXTRIN; ISOCHROMENE DERIVATIVE;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMICAL STRUCTURE; CHIRALITY; ELECTROOSMOSIS; ENANTIOSELECTIVITY; MICELLE; PH; SYNTHESIS;

EID: 46849084758     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826070802225304     Document Type: Article

References (22)

1. Potterat, O.; Zahner, H.; Volkmann, C.; Zeeck, A. Metabolic products of microorganisms. 264. Exfoliamycin and related metabolites, new naphthoquinone antibiotics from Streptomyces exfoliatus. J. Antibiot. 1993, 46, 346-349.
2. Poch, G.K.; Gloer, J.B. Obionin A: A new polyketide metabolite from the marine fungus Leptosphaeria obiones. Tetrahedron Lett. 1989, 30, 3483-3486.
3. Ali, S.; Read, R.W.; Sotheeswaran, S. Benzisochromanquinones and an isofuranonaphthoquinone from Ventilago vitiensis (Rhamnaceae). Phytochemistry 1994, 35, 1029-1032.
4. Hari, L.; De Buyck, L.F.; De Pooter, H.L. Naphthoquinoid pigments from Pentas longiflora. Phytochemistry 1991, 30, 1726-1727.
5. Naruse, N.; Goto, M.; Watanabe, Y.; Terasawa, T.; Dobashi, K. K1115 A, a new anthraquinone that inhibits the binding of activator protein-1 (AP-1) to its recognition sites. II. Taxonomy, fermentation, isolation, physico-chemical properties and structure determination. J. Antibiot. 1998, 51, 545-552.
6. Wang, W.; Breining, T.; Li, T.; Milburn, R.; Attardo, G. Dehydrogenation by air: preparation of 1,3-disubstituted-5,1-dioxo-5,10-dihydroxy- 1H-benzo[g]isochromene scaffold. Tetrahedron Lett. 1998, 39, 2459-2462.
7. Wang, W.; Li, T.; Miburn, R.; Yates, J.; Hinnant, E.; Luzzio, M.J.; Noble, S.A.; Attardo, G. Novel 1,3-disubstituted-5,10-dihydro-5,10-dioxo-1H- benzo[g] isochromene -3 carboxamides as potent antitumor agents. Bioorg. Med. Chem. Lett. 1998, 8, 1579-1584.
8. Mo, S.; Wang, S.; Zhou, G.; Yang, Y.; Li, Y.; Chen, X.; Shi, J. Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius. J. Nat. Prod. 2004, 67, 823-828.
9. Wei, W.; Zhang, Y.; Yao, Z. Efficient construction of novel α-keto spiro ketal and the total synthesis of (+/-)- terreinol. Tetrahedron Lett. 2005, 61, 11882-11886.
10. Mmutlane, E.M.; Michael, J.P.; Green, I.R.; de Koning, C.B. The synthesis of ventiloquinone L, the monomer of cardinalin 3. Org. Biomol. Chem. 2004, 2, 2461-2470.
11. Govender, S.; Mmutlane, E.M.; van Otterlo, Willem A.L.; de Koning, C.B. Bidirectional racemic synthesis of the biologically active quinone cardinalin 3. Org. Biomol. Chem. 2007, 5, 2433-2440.
12. Verin, S.V.; Tosunyan, D.E.; Kuznetsov, E.V. An efficient access to α-tetralones and their derivatives via σ-quinodimethanes generated by isochromene ring cleavage. Mendeleev Commun. 1992, 1, 20-21.
13. Krohn, K.; Vukics, K. First chemical synthesis of the antiviral agents S2502 and S2507. Synthesis 2007, 18, 2894-2900.
14. Yue, D.; Della Ca, N.; Larock, R.C. Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones. Org. Lett. 2004, 6, 1581-1584.
15. Lantz, A.W.; Rozhkov, R.V.; Larock, R.C.; Armstrong, D.W. Enantiomeric separation of neutral hydrophobic dihydrofuroflavones by cyclodextrin-modified micellar capillary electrophoresis. Electrophoresis 2004, 25, 2727-2734.
16. Bao, Y.; Lantz, A.W.; Yao, T.; Huang, Q.; Larock, R.C.; Armstrong, D.W. Enantiomeric separation of furan derivatives and fused polycycles by cyclodextrin-modified micellar capillary electrophoresis. Electrophoresis 2004, 25, 2727-2734.
17. Terabe, S.; Miyashita, Y.; Shibata, O.; Barnhart, E.R.; Alexander, L.R.; Patterson, D.G.; Karger, B.L.; Hosoya, K.; Tanaka, N. Separation of highly hydrophobic compounds by cyclodextrin-modified micellar electrokinetic chromatography. J. Chromatogr. A 1990, 516, 23-31.
18. Terabe, S.; Miyashita, Y.; Ishihama, Y.; Shibata, O. Cyclodextrin- modified micellar electrokinetic chromatography: separation of hydrophobic and enantiomeric compounds. J. Chromatogr. A 1993, 636, 47-55.
19. Nair, U.B.; Rundlet, K.L.; Armstrong, D.W. Determination of association constants in cyclodextrin or vancomycin-modified micellar capillary electrophoresis. J. Liq. Chromatogr. & Rel. Technol. 1997, 20, 203-216.
20. Nishi, H.; Fukuyama, T.; Terabe, S. Chiral separation by cyclodextrin-modified micellar electrokinetic chromatography. J. Chromatogr. 1991, 553, 503-516.
21. Terabe, S.; Otsuka, K.; Ando, T. Band broadening in electrokinetic chromatography with micellar solutions and open-tubular capillaries. Anal. Chem. 1989, 61, 251-260.
22. Armstrong, D.W.; Ward, T.J. Micellar effects on molecular diffusion: theoretical and chromatographic considerations. Anal. Chem. 1986, 58, 579-582.