Abstract
| - A novel method for preparation of multivalent oligonucleotide glycoconjugates on a solid support hasbeen described. A pentaerythritol-based phosphoramidite (1) bearing two masked aminooxy groupshas been used as the key building block. After conventional chain assembly, the aminooxy functionshave been deblocked by a hydrazinium acetate treatment and subsequently oximated with fullyacetylated 4-oxobutyl α-d-mannopyranoside. The conjugates obtained have been shown to withstandstandard ammonolytic deprotection and cleavage from the support. Four different oligonucleotideglycoconjugates containing two, four, or six α-d-mannopyranosyl units (12−15) have been preparedto demonstrate the applicability of the procedure. The glycosyl residues only moderately retardshybridization of the oligonucleotide moiety.
|