Carbohydrate-oligonucleotide conjugates

Curr Protoc Nucleic Acid Chem. 2009 Dec:Chapter 4:Unit4.38. doi: 10.1002/0471142700.nc0438s39.

Abstract

This unit describes a strategy for attaching two mannose and two galactose residues to an oligonucleotide. This conjugation can be performed at the 5'-end of the oligonucleotide sequence, using modified phosphoramidites. First, the oligonucleotide scaffold is synthesized on solid support using a DNA synthesizer, with commercially available and modified phosphoramidites. After the first "click" reaction with a galactosylated azide derivative on solid support, the bromine atoms are replaced with azides and a second click reaction is performed with propargylated mannose either on solid support or in solution. Additionally, using a monoalkynated solid support, the conjugation with carbohydrate residues can be performed at the 3'-end of the oligonucleotide according to a similar protocol. Curr. Protoc. Nucleic Acid Chem. 39:4.38.1-4.38.25.

MeSH terms

  • Azides / chemistry
  • Carbohydrates / chemistry
  • Galactose / chemistry*
  • Mannose / chemistry*
  • Oligonucleotides / chemistry*
  • Organophosphorus Compounds / chemistry

Substances

  • Azides
  • Carbohydrates
  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • Mannose
  • Galactose