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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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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). |
format | Online Article Text |
id | pubmed-7154675 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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