Staudinger Ligation

The reaction between an azide and a phosphine forming an aza-ylide was first reported in 1919 by Nobel Prize laureate Herrmann Staudinger. It has found widespread application in chemical synthesis, and is valuable as a highly chemoselective ligation method for the preparation of bioconjugates. Both reactive functionalities involved in the Staudinger ligation reaction are bioorthogonal and readily combine at room temperature in aqueous environments. These conditions make it possible to exploit the Staudinger ligation in complex cellular and organismal environments in the investigation of various processes in chemical biology. Sigma-Aldrich is happy to provide phosphine ligands for your various Staudinger ligation and conjugation applications.

Learn More about the Staudinger Ligation
Staudinger Ligation
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670359 Acetylthiomethyl-diphenylphosphine borane complex ≥98.0% C15H18BOPS
290734 Dabco® 33-LV C6H12N2
578282 1,4-Diazabicyclo[2.2.2]octane hydrochloride, polymer-bound 100-200 mesh, extent of labeling: ~2.0 mmol/g N loading, 1 % cross-linked with divinylbenzene  
679011 2-(Diphenylphosphino)terephthalic acid 1-methyl 4-pentafluorophenyl diester 97% C27H16F5O4P
715069 N-Succinimidyl 3-(diphenylphosphino)propionate 95% C19H18NO4P