Cyclopropenones and the photochemical generation of cyclic alkynes therefrom

US8426649B2 · kind B2 · utility

Assignee

• University of Georgia Research Foundation, Inc. · US

Inventors

• Vladimir V. Popik · Watkinsville, US
• Andrei A. Poloukhtine · Scottsdale, US
• Jason J. Locklin · Bogart, US
• Geert-Jan Boons · Athens, US
• Margaretha Wolfert · Athens, US
• Sara V. Orski · Gaithersburg, US

Key dates

• Filing date: Jul 14, 2011
• Grant date: Apr 23, 2013
• Expiry date: Jul 14, 2031

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/36
• WIPO field: Measurement
• WIPO sector: Instruments

Abstract

Cyclic alkynes (e.g., cyclooctynes such as dibenzocyclooctynes) can be photochemically generated from cyclopropenones as disclosed herein. The cyclic alkynes can be reacted (e.g., in situ) with materials having alkyne-reactive groups (e.g., azide groups in a “click” reaction). In preferred embodiments, the generation and reaction of the cyclic alkyne can proceed in the absence of a catalyst (e.g., Cu(I)). These reactions can be useful, for example, for the selective labeling of living cells that are metabolically modified with azido-containing surface monosaccharides, or for light-directed surface patterning.