Synthesis of aminooxy and N-alkylaminooxy amines for use in bioconjugation

J Org Chem. 2010 Aug 20;75(16):5757-9. doi: 10.1021/jo101066c.

Abstract

Five Boc-protected aminooxy and N-alkylaminooxy amines have been synthesized in 60-95% overall yield using a common synthetic strategy from readily available two- and three-carbon Cbz-protected amino alcohols. The amines can be linked to biomolecules via amide formation and incorporated directly into peptoids via submonomer synthesis. Subsequent deprotection of the aminooxy and N-alkylaminooxy groups enables conjugation with desired target molecules via established chemoselective ligation methods. The range of derivatives synthesized allows different distances to be established between the conjugated molecules.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry
  • Ligands
  • Molecular Structure
  • Peptoids / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Ligands
  • Peptoids