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Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations.

ABSTRACT: 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 ?Man, ?Fuc or ?Lac in an overall tetravalent presentation, and either 2:2 or 3:1 relative proportions, have been prepared.

SUBMITTER: Thomas B

PROVIDER: S-EPMC3326620 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations.

Thomas Baptiste B Fiore Michele M Bossu Isabelle I Dumy Pascal P Renaudet Olivier O

Beilstein journal of organic chemistry 20120320

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 presentatio ...[more]

PMID: 22509212

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