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Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes

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‐phosphor...

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Autores principales: Savicheva, Elizaveta A., Seikowski, Jan, Kast, Jeannette I., Grünig, Christoph R., Belov, Vladimir N., Hell, Stefan W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898655/
https://www.ncbi.nlm.nih.gov/pubmed/33245831
http://dx.doi.org/10.1002/anie.202013187
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author Savicheva, Elizaveta A.
Seikowski, Jan
Kast, Jeannette I.
Grünig, Christoph R.
Belov, Vladimir N.
Hell, Stefan W.
author_facet Savicheva, Elizaveta A.
Seikowski, Jan
Kast, Jeannette I.
Grünig, Christoph R.
Belov, Vladimir N.
Hell, Stefan W.
author_sort Savicheva, Elizaveta A.
collection PubMed
description 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.
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spelling pubmed-78986552021-03-03 Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes Savicheva, Elizaveta A. Seikowski, Jan Kast, Jeannette I. Grünig, Christoph R. Belov, Vladimir N. Hell, Stefan W. Angew Chem Int Ed Engl Research Articles 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. John Wiley and Sons Inc. 2020-12-21 2021-02-15 /pmc/articles/PMC7898655/ /pubmed/33245831 http://dx.doi.org/10.1002/anie.202013187 Text en © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Savicheva, Elizaveta A.
Seikowski, Jan
Kast, Jeannette I.
Grünig, Christoph R.
Belov, Vladimir N.
Hell, Stefan W.
Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes
title Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes
title_full Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes
title_fullStr Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes
title_full_unstemmed Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes
title_short Fluorescence Assisted Capillary Electrophoresis of Glycans Enabled by the Negatively Charged Auxochromes in 1‐Aminopyrenes
title_sort fluorescence assisted capillary electrophoresis of glycans enabled by the negatively charged auxochromes in 1‐aminopyrenes
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898655/
https://www.ncbi.nlm.nih.gov/pubmed/33245831
http://dx.doi.org/10.1002/anie.202013187
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