Solid-phase synthesis of multiantennary oligonucleotide glycoconjugates utilizing on-support oximation

: Katajisto J, Virta P, Lonnberg H

Publisher: AMER CHEMICAL SOC

: 2004

Bioconjugate Chemistry

BIOCONJUGATE CHEMISTRY

: BIOCONJUGATE CHEM

: 15

: 4

: 890

: 896

: 7

: 1043-1802

DOI: https://doi.org/10.1021/bc049955n

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.

Chemical sciences