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

ABSTRACT: 1-Aminopyrenes with three ?-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 (??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).

SUBMITTER: Savicheva EA

PROVIDER: S-EPMC7154675 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Savicheva Elizaveta A EA Mitronova Guyzel Yu GY Thomas Laura L Böhm Marvin J MJ Seikowski Jan J Belov Vladimir N VN Hell Stefan W SW

Angewandte Chemie (International ed. in English) 20200128 14

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<sup>-1</sup> cm<sup>-1</sup> ) 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, ...[more]

PMID: 31895495

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