1. Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes
- Author
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Elizaveta A. Savicheva, Vladimir N. Belov, Jan Seikowski, Stefan W. Hell, Christoph R. Grünig, and Jeannette I. Kast
- Subjects
Glycan ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Reductive amination ,Catalysis ,Capillary electrophoresis ,fluorescent probes ,chromophores ,donor–acceptor systems ,Research Articles ,Fluorescent Dyes ,chemistry.chemical_classification ,Sulfonyl ,Chromatography ,biology ,010405 organic chemistry ,Auxochrome ,General Medicine ,General Chemistry ,Electron acceptor ,Fluorescence ,Acceptor ,glycoconjugates ,0104 chemical sciences ,Electrophoresis ,chemistry ,electrophoresis ,biology.protein ,Research Article - Abstract
A compact and negatively charged acceptor group, N‐(cyanamino)sulfonyl, is introduced for dye design and its influence on the absorption and emission spectra of the “push–pull” chromophores is demonstrated with 1,3,6‐tris[(cyanamino)sulfonyl]‐8‐aminopyrene. The new sulfonamides, including O‐phosphorylated (3‐hydroxyazetidine)‐N‐sulfonyl, are negatively charged electron acceptors and auxochromes. 1‐Aminopyrenes decorated with the new sulfonamides have three or six negative charges (pH ≥8), low m/z ratios, high mobilities in an electric field, and yellow to orange emission. We labeled maltodextrin oligomers by reductive amination, separated the products by electrophoresis, and demonstrated their high brightness in a commercial DNA analyzer and the distribution of the emission signal among the detection channels., Negatively charged electron acceptors and auxochromes? New sulfonamides make it possible! 1‐Aminopyrenes decorated with the new sulfonamides had low m/z ratios and high mobility in an electric field. Their glycoconjugates with reducing sugars were separated and detected at sub‐picomolar concentration by multicolor emission in a DNA analyzer (see picture).
- Published
- 2020