Synthesis of carbohydrates carrying fluorescent naphthalimide groups

CARB 63

Ashley M. Dreis, dreisam@uwec.edu1, Andrew J. Wagner, wagneraj@uwec.edu2, and David E. Lewis, lewisd@uwec.edu1. (1) Department of Chemistry, University of Wisconsin-Eau Claire, Eau Claire, WI 54702, (2) Department of Chemisty, University of Wisconsin-Eau Claire, Eau Claire, WI 54701
4-Alkylamino-N-alkyl-1,8-naphthalimides are compounds that couple high fluorescence quantum yields and large Stokes shifts with low toxicity to living cells, resistance to bleaching, and resistance to quenching by paramagnetic transition metal ions or other paramagnetic species. This makes them attractive compounds for use in fluroescence microscopy. With a view to preparing more water-soluble fluorescent dyes that do not rely necessarily on charged groups for water solubility, we have begun the synthesis of dyes containing mono- and disaccharide units covalently bound to the naphthalimide group. The results of efforts to prepare the target aminonaphthalimide dyes by Williamson and Gabriel-type alkylations of halo derivatives of monosaccharides, by the Amadori rearrangement of saccharide iminium ions, and by olefin metathesis of saccharide allyl ethers will be presented, and the fluorescence properties of these dyes will be discussed.
 

General Posters
6:00 PM-8:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Carbohydrate Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007