The Staudinger reaction or Staudinger reduction is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces an iminophosphorane intermediate  . Combined with the hydrolysis of the aza-ylide to produce a phosphine oxide and an amine, this reaction is a mild method of reducing an azide to an amine. Triphenylphosphine is commonly used as the reducing agent, yielding triphenylphosphine oxide as the side product in addition to the amine.
The reaction was invented by and named after Hermann Staudinger.
Developed by Saxon and Bertozzi in 2000, the Staudinger ligation is a modification of the classical Staudinger reaction in which an electrophilic trap (usually a methyl ester) is appropriately placed on the triaryl phosphine . In the Staudinger ligation, the aza-ylide intermediate rearranges, in aqueous media, to produce an amide linkage and the phosphine oxide, and is so named the Staudinger ligation because it ligates the two molecules together, whereas in the classical Staudinger reaction, the two products are not covalently linked after hydrolysis.
The general schematic for the Staudinger ligation is shown below.
The Staudinger ligation has seen many applications in the field of chemical biology.
- ↑ Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
- ↑ Gololobov, Y. G. et al. Tetrahedron 1981, 37, 437.
- ↑ Preparation of 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene from Two Versatile 1,3,5-Tri(halosubstituted) 2,4,6-Triethylbenzene Derivatives Karl J. Wallace, Robert Hanes, Eric Anslyn, Jeroni Morey, Kathleen V. Kilway, Jay Siegeld Synthesis 2005: 2080-2083. (Abstract)
- ↑ Saxon, E.; Bertozzi, C.R. Science 2000, 287, 2007.
- ↑ Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation Kosiova I, Janicova A, Kois P Beilstein Journal of Organic Chemistry, 2006 2:23 ( 30 November 2006 ) doi:10.1186/1860-5397-2-23
- ↑ the nucleoside is based on deoxyuridine, the marker is a coumarin with a carboxyl group activated by HOBT
There is no pharmaceutical or device industry support for this site and we need your viewer supported Donations | Editorial Board | Governance | Licensing | Disclaimers | Avoid Plagiarism | Policies