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"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.
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https://hal.univ-lorraine.fr/hal-01494417
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Submitted on : Thursday, March 23, 2017 - 2:04:23 PM
Last modification on : Friday, February 26, 2021 - 3:24:02 PM

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Sandrine Lamandé-Langle, Charlotte Collet, Raphael Hensienne, Christine Vala, Francoise Chrétien, et al.. "Click" glycosylation of peptides through cysteine propargylation and CuAAC. Bioorganic and Medicinal Chemistry, Elsevier, 2014, 22 (23), pp.6672-6683. ⟨10.1016/j.bmc.2014.09.056⟩. ⟨hal-01494417⟩

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