Fluorescence assisted capillary electrophoresis of glycans enabled by the 
negatively charged auxochromes in 1-Aminopyrenes

Savicheva, E. A.; Seikowski, J.; Kast, J. I.; Grünig, C. R.; Belov, V. N.; Hell, S. W.

doi:10.1002/anie.202013187

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Fluorescence assisted capillary electrophoresis of glycans enabled by the negatively charged auxochromes in 1-Aminopyrenes

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Savicheva, E. A.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

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Seikowski, J.
Department of NanoBiophotonics, MPI for Biophysical chemistry, Max Planck Society;

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Belov, V. N.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Hell, S. W.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

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Citation

Savicheva, E. A., Seikowski, J., Kast, J. I., Grünig, C. R., Belov, V. N., & Hell, S. W. (2021). Fluorescence assisted capillary electrophoresis of glycans enabled by the negatively charged auxochromes in 1-Aminopyrenes. Angewandte Chemie International Edition, 60(7), 3720-3726. doi:10.1002/anie.202013187.

Cite as: https://hdl.handle.net/21.11116/0000-0009-4A9B-6

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.