Strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) for fast and activatable protein conjugation

Bioconjug Chem. 2015 Feb 18;26(2):257-61. doi: 10.1021/bc500534d. Epub 2015 Jan 15.

Abstract

A main challenge in the area of bioconjugation is to devise reactions that are both activatable and fast. Here, we introduce a temporally controlled reaction between cyclooctynes and 1,2-quinones, induced by facile oxidation of 1,2-catechols. This so-called strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) shows a remarkably high reaction rate when performed with bicyclononyne (BCN), outcompeting the well-known cycloaddition of azides and BCN by 3 orders of magnitude, thereby allowing a new level of orthogonality in protein conjugation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azides / chemistry
  • Catechols / chemistry*
  • Click Chemistry
  • Cyclization
  • Cycloaddition Reaction
  • Models, Molecular
  • Proteins / chemistry*
  • Quinones / chemistry*

Substances

  • Alkynes
  • Azides
  • Catechols
  • Proteins
  • Quinones
  • 1-octyne