New branched amino acids for high affinity dendrimeric DC-SIGN ligands

Publication date: Available online 26 December 2017
Source:Bioorganic & Medicinal Chemistry
Author(s): Laurent Cattiaux, Vanessa Porkolab, Franck Fieschi, Jean-Maurice Mallet
A branched amino acid was synthesized from methyl glucopyranoside; this amino acid presents three amino groups protected by Fmoc and one acid group and can be used in classic peptide synthesis. In parallel, similar azido terminated blocks were synthesized.Successive coupling reaction and deprotection afforded dendrimers with up to 27 azido functional groups. As an example of application, D-mannose and L-fucose residues were linked through CuAAC coupling and resulting glycodendrimers were evaluated in their interaction with DC-SIGN using SPR competition assay.

Graphical abstract

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