Monosaccharide-NAIM derivatives for D-, L-configurational analysis

Molecules

Volumn 16, Issue 1, 2011, Pages 652-664

  Lin, Chunchi ^a   Kuo, Chien Yuan ^a   Liao, Kuo Shiang ^a   Yang, Wen Bin ^a  

^a GENOMICS RESEARCH CENTER   (Taiwan)

Author keywords

2,3 Naphthalene diamine; Cyclodextrin; D , L monosaccharides; Enantioseparation; Ligand exchange capillary electrophoresis

Indexed keywords

MONOSACCHARIDE;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMISTRY; LIMIT OF DETECTION; STEREOISOMERISM;

ELECTROPHORESIS, CAPILLARY; LIMIT OF DETECTION; MONOSACCHARIDES; STEREOISOMERISM;

EID: 79251478776     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16010652     Document Type: Article

References (23)

1. Guttman, A. Analysis of monosaccharide composition by capillary electrophoresis. J. Chromatogr. A 1997, 763, 271-277.
2. Volpi, N.; Maccari, F.; Linhardt, R. J. Capillary electrophoresis of complex natural polysaccharides. Electrophoresis 2008, 29, 3095-3106.
3. Bertozzi, C. R.; Kiessling, L. L. Chemical glycobiology. Science 2001, 291, 2357-2364.
4. Price, N. P. J.; Bowman, M. J.; Gall, S. L.; Berhow, M. A.; Kendra, D. F.; Lerouge, P. Functionalized C-glycoside ketohydrazones: carbohydrate derivatives that retain the ring integrity of the terminal reducing sugar. Anal. Chem. 2010, 82, 2893-2899.
5. Colombeau, L.; Traoré, T.; Compain, P.; Martin, O. R. Metal-free one-pot oxidative amidation of aldoses with functionalized amines. J. Org. Chem. 2008, 73, 8647-8650.
6. Lin, C.; Hung, W. T.; Kuo, C. Y.; Liao, K. S.; Liu, Y. C.; Yang, W. B. I2-catalyzed oxidative condensation of aldoses with diamines: synthesis of aldo-naphthimidazoles for carbohydrate analysis. Molecules 2010, 15, 1340-1353.
7. Lin, C.; Lai, P. T.; Liao, K. S.; Hung, W. T.; Yang, W. B.; Fang, J. M. Using molecular iodine in direct oxidative condensation of aldoses with diamines: An improved synthesis of aldobenzimidazoles and aldo-naphthimidazoles for carbohydrate analysis. J. Org. Chem. 2008, 73, 3848-3853.
8. Ward, T. J.; Baker, B. A. Chiral separations. Anal. Chem. 2008, 80, 4363-4372.
9. Preinerstorfer, B.; Lämmerhofer, M.; Lindner, W. Advances in enantioselective separations using electromigration capillary techniques. Electrophoresis 2009, 30, 100-132.
10. Underberg, W. J.; Waterval, J. C. Derivatization trends in capillary electrophoresis: a update. Electrophoresis 2002, 23, 3922-3933.
11. Gübitz, G.; Schmid, M. G. Chiral separation by capillary electromigration techniques. J. Chromatogr. A 2008, 1204, 140-156.
12. Chankvetadze, B. Enantiomer migration order in chiral capillary electrophoresis. Electrophoresis 2002, 23, 4022-4035.
13. Honda, S.; Suzuki, S.; Taga, A. Analysis of carbohydrates as 1-phenyl-3-methyl-5-pyrazolone derivatives by capaillary/microchip electrophoresis and capillary electrochromatography. J. Pharm. Biomed. Anal. 2003, 30, 1689-1714.
14. Kodama, S.; Aizawa, S.; Taga, A.; Yamashita, T.; Kemmei, T.; Yamamoto, A.; Hayakawa, K. Simultaneous chiral resolution of monosaccharides as 8-aminonaphthalene-1, 3, 6-trisulfonate derivatives by ligand-exange CE using borate as a central ion of the chiral selector. Electrophoresis 2007, 28, 3930-3933.
15. Stefansson, M.; Novotny, M. Electrophoretic resolution of monosaccharide enantiomers in borateoligosaccharide complexation media. J. Am. Chem. Soc. 1993, 115, 11573-11580.
16. Kodama, S.; Aizawa, S.; Taga, A.; Yamashita, T.; Yamamoto, A. Chiral resolution of monosaccharides as 1-phenyl-3-methyl-5-pyrazolone derivatives by ligand-exchange CE using borate anion as a central ion of the chiral selector. Electrophoresis 2006, 27, 4730-4734.
17. Stalcup, A. M.; Agyei, N. M. Heparin: a chiral mobile-phase additive for capillary zone electrophoresis. Anal. Chem. 1994, 66, 3054-3059.
18. Kuhn, R.; Stoecklin, F.; Erni, F. Chiral separations by host-guest complexation with cyclodextrin and crown ether in capillary zone electrophoresis. Chromatographia 1992, 33, 32-36.
19. Clark, C. R.; Barksdale, J. M. Synthesis and liquid chromatographic evaluation of some chiral derivatizing agents for resolution of amine enantiomers. Anal. Chem. 1984, 56, 958-962.
20. Sun, X. X.; Sun, L. Z.; Aboul-Enein, Y. Chiral derivatization reagents for drug enantioseparation by high-performance liquid chromatography based upon pre-column derivatization and formation of diastereomers. Biomed. Chromatogr. 2001, 15, 116-132.
21. Lamari, F. N.; Kuhn, R.; Karamanos, N. K. Derivatization of carbohydrates for chromatographic, electrophoretic and mass spectrometric structure analysis. J. Chromatogr. 2003, 793, 15-36.
22. Tietze, L. F. Domino reactions in organic synthesis. Chem. Rev. 1996, 96, 115-136.
23. Chmberland, S.; Gruschow, S.; Sherman, D. H.; Willams, R. M. Synthesis of potential early-stage intermediates in the biosynthesis of FR900482 and mitomycin C. Org. Lett. 2009, 11, 791-794.