Cyclopropenones and the photochemical generation of cyclic alkynes therefrom

US8541625B2 · kind B2 · utility

Assignee

• University of Georgia Research Foundation, Inc. · US

Inventors

• Vladimir V. Popik · Watkinsville, US
• Andrei A. Poloukhtine · Scottsdale, US
• Geert-Jan Boons · Athens, US
• Margaretha Wolfert · Athens, US

Key dates

• Filing date: Aug 6, 2012
• Grant date: Sep 24, 2013
• Expiry date: Aug 6, 2032

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/36
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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.