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Alpha-hydroxy-beta-triazolo-tetrazole for Click-chemistry

Reference

08758-01

Patents status

European priority patent application filed on March 11th, 2016 and entitled “ALPHA-HYDROXY-BETA-TRIAZOLO-TETRAZOLES”

US priority patent application filed on March 11th, 2016 and entitled “ALPHA-HYDROXY-BETA-TRIAZOLO-TETRAZOLES”

Inventors

François COUTY; Bruno DROUILLAT; Pierre QUINODOZ; Karen WRIGHT

commercial status

Exclusive or non-exclusive license

Collaboration

Laboratory

Institut Lavoisier de Versailles (ILV)

http://www.ilv.uvsq.fr

UMR 8180, Versailles, France

Description

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)

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