Unsymmetrical bisazides for chemoselective sequential ligation
US8871940B2 · kind B2 · utility
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Key dates
| Filing date | Jul 15, 2013 |
| Grant date | Oct 28, 2014 |
| Priority date | — |
| Expiry date | Jul 15, 2033 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D403/06
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Unsymmetrical bisazides containing chelating and non-chelating azido groups undergo chemoselective three-component copper(I)-catalyzed azide-alkyne conjugation reactions with two different alkyne molecules. In conjunction with the reactivity gap between aromatic and aliphatic alkynes, a bistriazole molecule can be generated with an excellent regioselectivity by mixing two alkynes and a bisazide in a single reaction container. This method is applicable in aqueous solutions at neutral pH, which may lend utilities in bioconjugation applications.
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