Abstract
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.
Keywords:
Branched amino acid; DC-SIGN; Dendrimers; Glycoside; SPR.
Copyright © 2017 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemistry
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Amides / chemistry
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Amino Acids, Branched-Chain / chemistry*
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Amino Acids, Branched-Chain / metabolism
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Catalysis
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Cell Adhesion Molecules / chemistry
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Cell Adhesion Molecules / metabolism*
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Copper / chemistry
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Cycloaddition Reaction
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Dendrimers / chemical synthesis
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Dendrimers / chemistry*
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Dendrimers / metabolism
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Fucose / chemistry
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Humans
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Inhibitory Concentration 50
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Lectins, C-Type / chemistry
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Lectins, C-Type / metabolism*
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Ligands
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Mannose / chemistry
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Receptors, Cell Surface / chemistry
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Receptors, Cell Surface / metabolism*
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Surface Plasmon Resonance
Substances
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Alkynes
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Amides
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Amino Acids, Branched-Chain
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Cell Adhesion Molecules
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DC-specific ICAM-3 grabbing nonintegrin
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Dendrimers
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Lectins, C-Type
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Ligands
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Receptors, Cell Surface
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Fucose
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Copper
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Mannose