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

Bioorg Med Chem. 2018 Mar 1;26(5):1006-1015. doi: 10.1016/j.bmc.2017.12.036. Epub 2017 Dec 26.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Amides / chemistry
  • Amino Acids, Branched-Chain / chemistry*
  • Amino Acids, Branched-Chain / metabolism
  • Catalysis
  • Cell Adhesion Molecules / chemistry
  • Cell Adhesion Molecules / metabolism*
  • Copper / chemistry
  • Cycloaddition Reaction
  • Dendrimers / chemical synthesis
  • Dendrimers / chemistry*
  • Dendrimers / metabolism
  • Fucose / chemistry
  • Humans
  • Inhibitory Concentration 50
  • Lectins, C-Type / chemistry
  • Lectins, C-Type / metabolism*
  • Ligands
  • Mannose / chemistry
  • Receptors, Cell Surface / chemistry
  • Receptors, Cell Surface / metabolism*
  • Surface Plasmon Resonance

Substances

  • Alkynes
  • Amides
  • Amino Acids, Branched-Chain
  • Cell Adhesion Molecules
  • DC-specific ICAM-3 grabbing nonintegrin
  • Dendrimers
  • Lectins, C-Type
  • Ligands
  • Receptors, Cell Surface
  • Fucose
  • Copper
  • Mannose