Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites

Chem Commun (Camb). 2010 May 14;46(18):3176-8. doi: 10.1039/b926818a. Epub 2010 Mar 11.

Abstract

Unsymmetrical phosphites react efficiently in a Staudinger reaction with p-azido-phenylalanine, which can be applied for the biotinylation of proteins, thereby expanding the scope of the chemoselective Staudinger-phosphite reaction of aryl azides with symmetrical phosphites to the corresponding phosphoramidates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Biotinylation
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry
  • Phosphites / chemistry*
  • Proteins / chemistry*

Substances

  • Azides
  • Phosphites
  • Proteins
  • 4-azidophenylalanine
  • Phenylalanine