Elsevier

Carbohydrate Research

Volume 475, 1 March 2019, Pages 65-68
Carbohydrate Research

New lectin ligands: Testing of Amadori rearrangement products with a series of mannoside-specific lectins

https://doi.org/10.1016/j.carres.2019.01.010Get rights and content
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Highlights

  • Application of the Amadori Rearrangement for the synthesis of D-manno configured C-glycosyl type glycoconjugates.

  • Monovalent and multivalent Amadori rearrangement products as ligands for mannoside-specific lectins of various sources.

  • Synthesis of multivalent BSA-based C-glycosyl-type neoglycoconjugates.

Abstract

1-(N-Phenyl)amino-1-deoxy-α-D-manno-hept-2-ulose (2) and two multivalent BSA-based structures 7 and 8, d-manno-configured C-glycosyl-type compounds derived from an Amadori rearrangement, were evaluated as ligands for mannoside-specific lectins of various sources. The determination of the concentration corresponding to 50% of inhibition (IC50) is described. Multivalency turned out to effectively influence ligand selectivity and lectin binding.

Keywords

Carbohydrate-lectin interactions
Amadori rearrangement
C-Glycosyl-type glycoconjugates
Antiadhesives
Inhibition assay

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