Context

Click chemistry consists in synthezing chemicals via the assembly of smaller modular units. The invention relates more precisely to the CuAAC reaction ; copper(I)-catalysed azide-alkyne cycloaddition.

Technical description
The invention lies in the use of new compounds (alpha-hydroxy-beta tetrazoles) in click chemistry, allowing two ligations thanks to two successive CuAAC reactions.

The first ligation is made with molecule (1), then the alpha-hydroxy-tetrazole group is transformed into an alkyne by EDC (a water-soluble crosslinker) treatment. The second alkyne, called latent alkyne (2), is used for a second CuAAC reaction (3), allowing the addition of a second molecule.

The second alkyne being latent (not in the form of an alkyne during the first ligation) allows the grafting of a different molecule on the latter. This process can be seen as an orthogonal use of click chemistry.

Development stage

Various compounds already synthesized

Benefits

• Multiple reactivity of the alpha-hydroxy-beta tetrazole group
• Reaction at ambient temperature

Industrial applications

• Bioconjugation (ligation of chromophores on biomolecules)
• Photovoltaics (grafting of active compounds on surfaces)
• Medicinal chemistry (automated preparation of peptidomimtics on surfaces, thanks to the 1,4-triazole which is a peptidic bond analog)