Amine-selective bioconjugation using arene diazonium salts

Org Lett. 2014 Aug 1;16(15):3908-11. doi: 10.1021/ol5016509. Epub 2014 Jul 14.

Abstract

A novel bioconjugation strategy is presented that relies on the coupling of diazonium terephthalates with amines in proteins. The diazonium captures the amine while the vicinal ester locks it through cyclization, ensuring no reversibility. The reaction is highly efficient and proceeds under mild conditions and short reaction times. Densely functionalized, complex natural products were directly coupled to proteins using low concentrations of coupling partners.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Cyclization
  • Diazonium Compounds / chemistry*
  • Molecular Structure
  • Proteins / chemistry*

Substances

  • Amines
  • Diazonium Compounds
  • Proteins