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

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

Author information

1
Laboratoire des Biomolécules, Département de chimie, École normale supérieure, PSL Research University, Sorbonne Universités, UPMC Univ. Paris 06, CNRS, 24 rue Lhomond, 75005 Paris, France.
2
Univ. Grenoble Alpes, CNRS, CEA, Institut de Biologie Structurale, Avenue des Martyrs, F-38044 Grenoble, France.
3
Laboratoire des Biomolécules, Département de chimie, École normale supérieure, PSL Research University, Sorbonne Universités, UPMC Univ. Paris 06, CNRS, 24 rue Lhomond, 75005 Paris, France. Electronic address: jean-maurice.mallet@ens.fr.

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

PMID:
29428526
DOI:
10.1016/j.bmc.2017.12.036
[Indexed for MEDLINE]

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