2. Academic Validation
  3. 'Click' glycosylation of peptides through cysteine propargylation and CuAAC

'Click' glycosylation of peptides through cysteine propargylation and CuAAC

  • Bioorg Med Chem. 2014 Dec 1;22(23):6672-6683. doi: 10.1016/j.bmc.2014.09.056.
Sandrine Lamandé-Langle 1,  Charlotte Collet 2,  Raphaël Hensienne 3,  Christine Vala 3,  Françoise Chrétien 3,  Yves Chapleur 2,  Amel Mohamadi 4,  Patrick Lacolley 4,  Véronique Regnault 4
Affiliations

Affiliations

  • 1 Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; CNRS, UMR 7565, F-54506 Vandoeuvre les Nancy, France. Electronic address: Sandrine.langle@univ-lorraine.fr.
  • 2 Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; CNRS, UMR 7565, F-54506 Vandoeuvre les Nancy, France; CHU de Nancy, Nancyclotep, 3 Rue du Morvan, F-54500 Vandoeuvre les Nancy, France.
  • 3 Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; CNRS, UMR 7565, F-54506 Vandoeuvre les Nancy, France.
  • 4 Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; INSERM U1116, 9 av. de la forêt de Haye, F-54500 Vandoeuvre-les-Nancy, France.
PMID: 25457125 DOI: 10.1016/j.bmc.2014.09.056
Abstract

'Click' glycosylation of cysteine-containing Peptides were carried out in good yield by Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC). For that Peptides were functionalized though direct propargylation of the cysteine residue allowing their use in CuAAC with suitable free or protected azido sugars of gluco, manno and galacto configuration. Among these free and protected glycopeptides a series of 'glycoRGD' Peptides were obtained and submitted to in vitro platelet aggregation tests, showing that the pseudoglycosylation of the adhesion sequence lowers the IC50 value and thus could improve the in vivo pharmacokinetic properties.

Keywords

Click chemistry; CuAAC; Glycoconjugate; Peptide; RGD.

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