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  Negatively charged yellow-emitting 1-aminopyrene dyes for reductive amination and fluorescence detection of glycans.

Belov, V. N., Savicheva, E. A., Mitronova, G., Thomas, L., Böhm, M. J., Seikowski, J., et al. (2020). Negatively charged yellow-emitting 1-aminopyrene dyes for reductive amination and fluorescence detection of glycans. Angewandte Chemie International Edition, 59(14), 5505-5509. doi:10.1002/anie.201908063.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-75FD-B Version Permalink: http://hdl.handle.net/21.11116/0000-0006-9F10-5
Genre: Journal Article

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 Creators:
Belov, V. N.1, Author              
Savicheva, E. A.1, Author              
Mitronova, G.1, Author              
Thomas, L., Author
Böhm, M. J.1, Author              
Seikowski, J.2, Author              
Hell, S. W.1, Author              
Affiliations:
1Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society, ou_578627              
2Research Group of Nucleic Acid Chemistry, MPI for Biophysical Chemistry, Max Planck Society, ou_578605              

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Free keywords: Donor-acceptor systems; Glycoconjugates; chromophores; electrophoresis; fluorescent probes
 Abstract: 1 - Aminopyrenes with three w-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 ~ 20000 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 (in respect of brightness and electrophoretic mobilities) the corresponding APTS derivatives (benchmark dye with green emission in conjugates).

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Language(s): eng - English
 Dates: 2020-01-022020-03-27
 Publication Status: Published in print
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 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201908063
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Title: Angewandte Chemie International Edition
Source Genre: Journal
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Pages: - Volume / Issue: 59 (14) Sequence Number: - Start / End Page: 5505 - 5509 Identifier: -