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  • Title: Solid-phase synthesis of multiantennary oligonucleotide glycoconjugates utilizing on-support oximation.
    Author: Katajisto J, Virta P, Lönnberg H.
    Journal: Bioconjug Chem; 2004; 15(4):890-6. PubMed ID: 15264878.
    Abstract:
    A novel method for preparation of multivalent oligonucleotide glycoconjugates on a solid support has been described. A pentaerythritol-based phosphoramidite (1) bearing two masked aminooxy groups has been used as the key building block. After conventional chain assembly, the aminooxy functions have been deblocked by a hydrazinium acetate treatment and subsequently oximated with fully acetylated 4-oxobutyl alpha-D-mannopyranoside. The conjugates obtained have been shown to withstand standard ammonolytic deprotection and cleavage from the support. Four different oligonucleotide glycoconjugates containing two, four, or six alpha-D-mannopyranosyl units (12-15) have been prepared to demonstrate the applicability of the procedure. The glycosyl residues only moderately retards hybridization of the oligonucleotide moiety.
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