Bertozzi-Staudinger ligation

Fig. 2 Ligation reactions used in two-step ABPP using the azide functionality as ligation handle (a) Staudinger-Bertozzi ligation, (b) Cu(I)-catalyzed click reaction, (c) copper-free click reaction, and (d) photoclick reaction...

Experimental protocol for Staudinger-Bertozzi, Cu(l)-catalyzed Huisgen alkyne-azide cycloaddition, and reverse-electron-demand Diels-Alder ligation to distinguish between pi, p2,and p5. 

Kiick, K.L., Saxon, E., Tirrell, D.A., and Bertozzi, C.R. (2002) Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proc. Natl Acad. Sci. USA 99, 19-24. 

So far, the methods that have been shown to enable chemoselective peptide bond formation have relied upon the particular reactivity between thioesters and aminothiols. Almost simultaneously, Raines [36] and Bertozzi [37] reported a new method for the formation of a peptide bond with high chemoselectivity the so-called Staudinger ligation. This reaction had... 

Saxon E, Armstrong JI, Bertozzi CR. A traceless Staudinger ligation for the chemoselective synthesis of amide bonds. Org.Lett. 2000 2 2141-2143. 

Prescher, J. A., Dube, D. H., Bertozzi, C. R. (2003). Probing azido sugar metabolism in vivo using the Staudinger ligation. Glycobiology, 13, 894. 

It is important to cite several other recently developed methods for peptide ligation, which include the traceless Staudinger ligations of Bertozzi [62], Raines [63], and their co-workers, the decarboxylative amide ligation (KAHA ligation) developed by Bode et al. [64], and the Ser/Thr ligation of Li et al. [65, 66]. While these methods can be considered complementary to NCL, they have various constraints which limit their general utility. 

In another example, Raines and Bertozzi and their co-workers modified the Staudinger reaction to an amide-b(Mid-forming ligation, which utilizes a C-terminal phosphinobenzenethioester and an N-terminal a-azide (Scheme 11). 

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