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BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides
Author(s) -
Uriel Clara,
Permingeat Caterina,
Ventura Juan,
AvellanalZaballa Edurne,
Bañuelos Jorge,
GarcíaMoreno Inmaculada,
Gómez Ana M.,
Lopez J. Cristobal
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905780
Subject(s) - bodipy , fluorescence , chemistry , glycosylation , fluorophore , chromophore , glycosidic bond , glycosyl , combinatorial chemistry , moiety , context (archaeology) , photochemistry , biochemistry , organic chemistry , paleontology , physics , quantum mechanics , biology , enzyme
A series of fluorescent boron‐dipyrromethene (BODIPY, 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐ s ‐indacene) dyes have been designed to participate, as aglycons, in synthetic oligosaccharide protocols. As such, they served a dual purpose: first, by being incorporated at the beginning of the process (at the reducing‐end of the growing saccharide moiety), they can function as fluorescent glycosyl tags, facilitating the detection and purification of the desired glycosidic intermediates, and secondly, the presence of these chromophores on the ensuing compounds grants access to fluorescently labeled saccharides. In this context, a sought‐after feature of the fluorescent dyes has been their chemical robustness. Accordingly, some BODIPY derivatives described in this work can withstand the reaction conditions commonly employed in the chemical synthesis of saccharides; namely, glycosylation and protecting‐group manipulations. Regarding their photophysical properties, the BODIPY‐labeled saccharides obtained in this work display remarkable fluorescence efficiency in water, reaching quantum yield values up to 82 %, as well as notable lasing efficiencies and photostabilities.