Hetero-Click Conjugation of Oligonucleotides with Glycosides Using Bifunctional Phosphoramidites

Two phosphoramidite derivatives, 1 and 2, each bearing two orthogonal functions: alkyne/thioacetyl or alkyne/tosyl, respectively, were synthesized and used to generate heteroglyco 5′‐oligonucleotide conjugates. After coupling, the first conjugation was performed using CuAAC on solid support with an...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-05, Vol.2015 (13), p.2921-2927
Main Authors: Meyer, Albert, Noël, Mathieu, Vasseur, Jean-Jacques, Morvan, François
Format: Article
Language:English
Subjects:
Carbohydrates
Chemical Sciences
Click chemistry
Glycoclusters
Glycoconjugates
Oligonucleo­tides
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Summary:Two phosphoramidite derivatives, 1 and 2, each bearing two orthogonal functions: alkyne/thioacetyl or alkyne/tosyl, respectively, were synthesized and used to generate heteroglyco 5′‐oligonucleotide conjugates. After coupling, the first conjugation was performed using CuAAC on solid support with an azide‐bearing carbohydrate. For 1, the second conjugation was performed in solution by a thiol “click” reaction using a bromoacetamide galactoside, whereas for 2, the tosyl group was converted into an azide and a second CuAAC was applied on solid support. Accordingly, a deoxycholic‐centered heteroglycocluster exhibiting two D‐galactose and two L‐fucose motifs, conjugated to an oligonucleotide, was successfully synthesized. Heteroglycoclusters were synthesized using orthogonal hetero‐click reactions involving i) CuI azide alkyne cycloadditions (CuAAC) and thiolation of bromoacetamide groups or ii) two successive CuAACs.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500165