Staudinger Ligation in Living Animals

Key words

Staudinger ligation - metabolic oligosaccharide engineering - bioorthogonal reaction - azides - phosphines

Significance

Chemical modification of cell-surface glycans in living animals provides a means to study these biopolymers within their native environment. The Staudinger ligation is a bioorthogonal reaction that can be carried out in the whole ­organism. This reaction is frequently used for the study of lipids, steroids, and cofactors.

Comment

Bertozzi and co-workers demonstrated the Staudinger ligation of an azide (SiaNAz) and a functionalized phosphine (Phos-Flag) in living mice. The azide was delivered to cell-surface glycoconjugates by metabolism of ManNAz to SiaNAz. The ligation in mice tissue was detected using fluorescein isothiocyanate-labelled anti-Flag antibodies followed by flow cytometry analysis.