11-Azidoundecanoic acid is a click chemistry reagent containing an azide group. 11-Azidoundecanoic acid acts as a hydrophobic bioconjugation linker that can be further modified at the azido-position using Staudinger ligation or Click-chemistry. 11-Azidoundecanoic acid is substrate of lipoic acid ligase (LpIA) for labeling[1][2].
The microbial lipoic acid ligase (LplA) can specifically attach an alkyl azide onto an engineered LplA acceptor peptide (LAP). Then the alkyl azide selectively derivatizes with cyclooctyne conjugates to various probes[1].
LplA method should provide general access to biochemical and imaging studies of cell surface proteins, using small fluorophores introduced via a short peptide tag[1].
[1]. FernÁndez-SuÁrez M, et al. Redirecting lipoic acid ligase for cell surface protein labeling with small-molecule probes. Nat Biotechnol. 2007 Dec;25(12):1483-7.
[2]. Heal WP, et al. N-Myristoyl transferase-mediated protein labelling in vivo. Org Biomol Chem. 2008 Jul 7;6(13):2308-15.