Copper-catalysed ligation of azides and acetylenes
AssigneeThe Scripps Research Institute
InventorsK. Barry Sharpless, Valery Fokin, Vsevold A. Rostovtsev, Luke Green, Fahmi Himo
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Abstract
A copper catalyzed click chemistry ligation process is employed to bind azides and terminal acetylenes to provide 1,4-disubstituted 1,2,3-triazole triazoles. The process comprises contacting an organic azide and a terminal alkyne with a source of reactive Cu(I) ion in human blood plasma to form by cycloaddition a 1,4-disubstituted 1,2,3-triazole. The source of reactive Cu(I) ion can be, for example, a Cu(I) salt, Cu(II) ion in the presence of a reducing agent, or copper metal.
Claims20
A copper catalyzed process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
- contacting a solution of an organic azide and a terminal alkyne with a source of catalytic Cu(I) ion and a ligand for Cu(I) to form a 1,4-disubstituted 1,2,3-triazole, wherein the solution comprises at least one solvent selected from the group consisting of water, a nitrile, and an alcohol.
A copper catalyzed process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
- contacting an aqueous solution of an organic azide and a terminal alkyne with a source of catalytic Cu(I) ion to form a 1,4-disubstituted 1,2,3-triazole, wherein the source of catalytic Cu(I) ion comprises Cu(II) ion subjected to a reducing electrochemical potential sufficient to generate Cu(I) ion therefrom.
A two-step process for derivatizing an amine-containing molecule with a triazole comprising the steps of:
- derivatizing an amino group of an amine-containing molecule with a terminal alkyne moiety to form an amino-substituted terminal alkyne;
- and
- contacting a solution of the amino-substituted terminal alkyne with an organic azide in the presence of a source of catalytic Cu(I) ion to form a 1,4-disubstituted 1,2,3-triazole derivative therefrom.
Dependencies are inferred from the claim text.