The chemoselective introduction of fluorinated moieties into biologically relevant scaffolds is now an established strategy to modulate and to study the properties of molecular leads. In this article we propose, for the first time, the diversity oriented synthesis of multivalent glycomimetics incorporating hexafluorovaline through a straightforward multicomponent sequential process, which occurs with high yield and in mild conditions. The same process has been successfully applied to the chemistry of aminoglycosides producing a neomycin-hexafluorovaline-galactose conjugate and providing a general, efficient strategy to functionalized aminoglycosides with sugar-hexafluorovaline tags.

Multicomponent diversity oriented synthesis of multivalent glycomimetics containing hexafluorovaline / M.C. Bellucci, S. A., S. M., V. A.. - In: TETRAHEDRON. - ISSN 0040-4020. - 71:40(2015), pp. 7630-7637. [10.1016/j.tet.2015.07.070]

Multicomponent diversity oriented synthesis of multivalent glycomimetics containing hexafluorovaline

M.C. Bellucci
Primo
;
2015

Abstract

The chemoselective introduction of fluorinated moieties into biologically relevant scaffolds is now an established strategy to modulate and to study the properties of molecular leads. In this article we propose, for the first time, the diversity oriented synthesis of multivalent glycomimetics incorporating hexafluorovaline through a straightforward multicomponent sequential process, which occurs with high yield and in mild conditions. The same process has been successfully applied to the chemistry of aminoglycosides producing a neomycin-hexafluorovaline-galactose conjugate and providing a general, efficient strategy to functionalized aminoglycosides with sugar-hexafluorovaline tags.
Aminoglycoside; Diversity oriented synthesis; Fluorine; Multicomponent synthesis; Multivalent glycomimetic; Biochemistry; Organic Chemistry; Drug Discovery; Pharmaceutical Science
Settore CHIM/06 - Chimica Organica
2015
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/423977
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