New solid support for the synthesis of 3'-oligonucleotide conjugates through glyoxylic oxime bond formation

Org Lett. 2007 Jan 18;9(2):219-22. doi: 10.1021/ol062607b.

Abstract

A novel solid support 1 was synthesized to incorporate glyoxylic aldehyde functionality at the oligonucleotide 3'-terminus. 6-mer and 11-mer oligonucleotide sequences containing 3'-glyoxylic aldehyde functionality were prepared by using this support. These modified oligonucleotides were coupled to reporters containing an aminooxy group to prepare oligonucleotide 3'-conjugates through glyoxylic oxime bond formation. The hydrolytic stability of a glyoxylic oxime linkage was also investigated. [reaction: see text].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques / methods*
  • Glyoxylates / chemical synthesis
  • Glyoxylates / chemistry*
  • Molecular Structure
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry
  • Oximes / chemical synthesis
  • Oximes / chemistry*
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Stereoisomerism

Substances

  • Glyoxylates
  • Oligonucleotides
  • Oximes
  • Peptides