New carbamate supports for the preparation of 3'-amino-modified oligonucleotides

Bioorg Med Chem. 1996 Oct;4(10):1649-58. doi: 10.1016/0968-0896(96)00156-3.

Abstract

A novel approach for the preparation of oligonucleotides carrying amino groups at the 3'-end is described. Several CPG supports having aminoalkyl groups and 3'-amino-2',3'-dideoxynucleosides linked through base-labile carbamate linkages such as 2-(2-nitrophenyl)ethoxycarbonyl and fluorenylmethoxycarbonyl were prepared using two different strategies. These supports are compatible to the standard solid phase phosphite-triester methodology and yield oligonucleotides containing amino groups at the 3'-end. Several properties of the 3'-amino oligonucleotides, such as nuclease resistance, hybridization, and preparation of oligonucleotide conjugates are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbamates / chemistry*
  • Chromatography, High Pressure Liquid
  • Dexamethasone
  • Dideoxynucleosides / chemistry*
  • Fluorescein
  • Fluoresceins
  • Mass Spectrometry
  • Oligonucleotides / chemical synthesis*

Substances

  • Carbamates
  • Dideoxynucleosides
  • Fluoresceins
  • Oligonucleotides
  • Dexamethasone
  • Fluorescein