Abstract
A convergent synthetic route to a tetrasaccharide related to PI-88, which allows the incorporation of a fluorescent BODIPY-label at the reducing-end, has been developed. The strategy, which features the use of 1,2-methyl orthoesters (MeOEs) as glycosyl donors, illustrates the usefulness of suitably-designed BODIPY dyes as glycosyl labels in synthetic strategies towards fluorescently-tagged oligosaccharides.
Highlights
The recognition of the crucial role of heparanase enzyme, an endo-β-D-glucuronidase able to degrade heparan sulfate (HS) in the extracellular matrix and basement membranes, in a number of pathological processes, such as metastasis and angiogenesis, has triggered the development of heparanase inhibitors [1,2,3,4,5,6]
Fluorescent labeling of biomolecules has been recognized as a research topic of great significance, since such labeling facilitates the investigation of glycoconjugates and their interaction in biological systems at high sensitivity [8,9,10,11,12]
We thought it would be of interest to investigate the feasibility of a synthetic approach to BODIPY-labeled PI-88 saccharide components, where the fluorescent dye is incorporated from the beginning of the synthetic sequence
Summary
The recognition of the crucial role of heparanase enzyme, an endo-β-D-glucuronidase able to degrade heparan sulfate (HS) in the extracellular matrix and basement membranes, in a number of pathological processes, such as metastasis and angiogenesis, has triggered the development of heparanase inhibitors [1,2,3,4,5,6]. Several reasons can be cited for this preference: their high fluorescent quantum yields (∅), excellent photochemical and chemical stabilities, and, arguably, the relatively facile modulation of their photophysical and/or chemical properties by means of synthetic postfunctionalization of their indacene core [13,14,15,16,17,18] Based on these precedents, we thought it would be of interest to investigate the feasibility of a synthetic approach to BODIPY-labeled PI-88 saccharide components, where the fluorescent dye is incorporated from the beginning of the synthetic sequence. In light of some reported literature precedents [20], the incorporation of the lipophilic BODIPY core to the saccharidic ensemble could lead to ameliorated biological activity in the ensuing saccharides In this Article, we report a synthetic approach to a PI-88 tetrasaccharide analogue [21] featuring the use of 1,2-methyl orthoester (MeOE).
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