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Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans

1‐Aminopyrenes with three ω‐hydroxylated N‐alkylsulfonamido or alkylsulfonyl residues in positions 3, 6, and 8 were prepared, O‐phosphorylated, and applied for reductive amination of oligosaccharides. The dyes (ϵ≈20 000 m (−1) cm(−1)) with six negative charges (pH≥8) and low m/z ratios enable labeli...

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Autores principales: Savicheva, Elizaveta A., Mitronova, Guyzel Yu., Thomas, Laura, Böhm, Marvin J., Seikowski, Jan, 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/PMC7154675/
https://www.ncbi.nlm.nih.gov/pubmed/31895495
http://dx.doi.org/10.1002/anie.201908063
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author Savicheva, Elizaveta A.
Mitronova, Guyzel Yu.
Thomas, Laura
Böhm, Marvin J.
Seikowski, Jan
Belov, Vladimir N.
Hell, Stefan W.
author_facet Savicheva, Elizaveta A.
Mitronova, Guyzel Yu.
Thomas, Laura
Böhm, Marvin J.
Seikowski, Jan
Belov, Vladimir N.
Hell, Stefan W.
author_sort Savicheva, Elizaveta A.
collection PubMed
description 1‐Aminopyrenes with three ω‐hydroxylated N‐alkylsulfonamido or alkylsulfonyl residues in positions 3, 6, and 8 were prepared, O‐phosphorylated, and applied for reductive amination of oligosaccharides. The dyes (ϵ≈20 000 m (−1) cm(−1)) with six negative charges (pH≥8) and low m/z ratios enable labeling and fluorescence detection of reducing sugars (glycans) related to the most structurally and functionally diverse class of natural products. Under excitation with a 488 nm laser, the new glycoconjugates emit yellow light of about 560 nm, outperforming (with respect to brightness and faster electrophoretic mobilities) the corresponding APTS derivatives (benchmark dye with green emission in conjugates).
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spelling pubmed-71546752020-04-14 Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans Savicheva, Elizaveta A. Mitronova, Guyzel Yu. Thomas, Laura Böhm, Marvin J. Seikowski, Jan Belov, Vladimir N. Hell, Stefan W. Angew Chem Int Ed Engl Communications 1‐Aminopyrenes with three ω‐hydroxylated N‐alkylsulfonamido or alkylsulfonyl residues in positions 3, 6, and 8 were prepared, O‐phosphorylated, and applied for reductive amination of oligosaccharides. The dyes (ϵ≈20 000 m (−1) cm(−1)) with six negative charges (pH≥8) and low m/z ratios enable labeling and fluorescence detection of reducing sugars (glycans) related to the most structurally and functionally diverse class of natural products. Under excitation with a 488 nm laser, the new glycoconjugates emit yellow light of about 560 nm, outperforming (with respect to brightness and faster electrophoretic mobilities) the corresponding APTS derivatives (benchmark dye with green emission in conjugates). John Wiley and Sons Inc. 2020-01-28 2020-03-27 /pmc/articles/PMC7154675/ /pubmed/31895495 http://dx.doi.org/10.1002/anie.201908063 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. 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 Communications
Savicheva, Elizaveta A.
Mitronova, Guyzel Yu.
Thomas, Laura
Böhm, Marvin J.
Seikowski, Jan
Belov, Vladimir N.
Hell, Stefan W.
Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans
title Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans
title_full Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans
title_fullStr Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans
title_full_unstemmed Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans
title_short Negatively Charged Yellow‐Emitting 1‐Aminopyrene Dyes for Reductive Amination and Fluorescence Detection of Glycans
title_sort negatively charged yellow‐emitting 1‐aminopyrene dyes for reductive amination and fluorescence detection of glycans
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7154675/
https://www.ncbi.nlm.nih.gov/pubmed/31895495
http://dx.doi.org/10.1002/anie.201908063
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