An aminooxy-functionalized non-nucleosidic phosphoramidite for the construction of multiantennary oligonucleotide glycoconjugates on a solid support

Curr Protoc Nucleic Acid Chem. 2005 Jul:Chapter 4:Unit 4.26. doi: 10.1002/0471142700.nc0426s21.

Abstract

In this unit, a method is described that allows construction of multiantennary oligonucleotide glycoconjugates on a solid support. A bis(hydroxymethyl)malondiamide-based phosphoramidite that contains two phthaloyl-protected aminooxy groups compatible with normal chain assembly is prepared. The aminooxy functions can be deblocked with a hydrazinium acetate treatment and subsequently oximated on-support with fully acetylated 4-oxobutyl alpha-D-mannopyranoside. The resulting reagent is then used to prepare a conjugate containing two non-nucleosidic building blocks (i.e., four alpha-D-mannopyranosyl units) close to the 5' terminus of the oligonucleotide.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Glycoconjugates / chemical synthesis*
  • Glycoconjugates / chemistry
  • Mannose / chemistry
  • Mannose / metabolism
  • Molecular Structure
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Organophosphorus Compounds / chemistry*

Substances

  • Glycoconjugates
  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • Mannose