title: 'Click' glycosylation of peptides through cysteine propargylation and CuAAC.
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.
authors.affiliation: 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.
authors.forename: Sandrine
authors.initials: S
authors.lastname: Lamandé-Langle
authors.affiliation: 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.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Collet
authors.affiliation: Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; CNRS, UMR 7565, F-54506 Vandoeuvre les Nancy, France.
authors.forename: Raphaël
authors.initials: R
authors.lastname: Hensienne
authors.affiliation: Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; CNRS, UMR 7565, F-54506 Vandoeuvre les Nancy, France.
authors.forename: Christine
authors.initials: C
authors.lastname: Vala
authors.affiliation: Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; CNRS, UMR 7565, F-54506 Vandoeuvre les Nancy, France.
authors.forename: Françoise
authors.initials: F
authors.lastname: Chrétien
authors.affiliation: 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.
authors.forename: Yves
authors.initials: Y
authors.lastname: Chapleur
authors.affiliation: Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; INSERM U1116, 9 av. de la forêt de Haye, F-54500 Vandoeuvre-les-Nancy, France.
authors.forename: Amel
authors.initials: A
authors.lastname: Mohamadi
authors.affiliation: Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; INSERM U1116, 9 av. de la forêt de Haye, F-54500 Vandoeuvre-les-Nancy, France.
authors.forename: Patrick
authors.initials: P
authors.lastname: Lacolley
authors.affiliation: Université de Lorraine, F-54500 Vandoeuvre-les-Nancy, France; INSERM U1116, 9 av. de la forêt de Haye, F-54500 Vandoeuvre-les-Nancy, France.
authors.forename: Véronique
authors.initials: V
authors.lastname: Regnault
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D003545:Cysteine / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010974:Platelet Aggregation / Q000187:drug effects
chemical_list: D000480:Alkynes; D001386:Azides; D009942:Organometallic Compounds; D010455:Peptides; D003300:Copper; D010293:Pargyline; D003545:Cysteine
keywords: Click chemistry; CuAAC; Glycoconjugate; Peptide; RGD