Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

Synthetic heteroglycoclusters are being subjected to increasing interest due to their potential to serve as selective ligands for carbohydrate-binding proteins. In this paper, we describe an expedient strategy to prepare cyclopeptides displaying well-defined distributions and combinations of carbohy...

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Bibliographic Details
Main Authors: Baptiste Thomas, Michele Fiore, Isabelle Bossu, Pascal Dumy, Olivier Renaudet
Format: Article
Language:English
Published: Beilstein-Institut 2012-03-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
chemoselective ligation
click chemistry
cyclopeptide
heteroglycocluster
oxime
Online Access:https://doi.org/10.3762/bjoc.8.47
Description
Summary:Synthetic heteroglycoclusters are being subjected to increasing interest due to their potential to serve as selective ligands for carbohydrate-binding proteins. In this paper, we describe an expedient strategy to prepare cyclopeptides displaying well-defined distributions and combinations of carbohydrates. By using both oxime ligation and copper(I)-catalyzed alkyne–azide cycloaddition, two series of compounds bearing binary combinations of αMan, αFuc or βLac in an overall tetravalent presentation, and either 2:2 or 3:1 relative proportions, have been prepared.
ISSN:1860-5397

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