Login / Signup

Fast and pH-Independent Elimination of trans-Cyclooctene by Using Aminoethyl-Functionalized Tetrazines.

Alexi J C SarrisThomas HansenMark A R de GeusElmer MauritsWard DoelmanHerman S OverkleeftJeroen D C CodéeDmitri V FilippovSander I van Kasteren
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)
The inverse-electron-demand Diels-Alder/pyridazine elimination tandem reaction, in which the allylic substituent on trans-cyclooctene is eliminated following reaction with tetrazines, is gaining interest as a versatile bioorthogonal process. One potential shortcoming of such currently used reactions is their propensity to proceed faster and more efficiently at lower pH, a feature caused by the nature of the tetrazines used. Here, we present aminoethyl-substituted tetrazines as the first pH-independent reagents showing invariably fast elimination kinetics at all biologically relevant pH values.
Keyphrases
  • machine learning
  • deep learning
  • molecular docking
  • mass spectrometry
  • electron transfer
  • liquid chromatography