421547-21-9Relevant articles and documents
Optimized aqueous Kinugasa reactions for bioorthogonal chemistry applications
Bilodeau, Didier A.,Margison, Kaitlyn D.,Ahmed, Noreen,Strmiskova, Miroslava,Sherratt, Allison R.,Pezacki, John Paul
supporting information, p. 1988 - 1991 (2020/02/25)
Kinugasa reactions hold potential for bioorthogonal chemistry in that the reagents can be biocompatible. Unlike other bioorthogonal reaction products, β-lactams are potentially reactive, which can be useful for synthesizing new biomaterials. A limiting factor for applications consists of slow reaction rates. Herein, we report an optimized aqueous copper(i)-catalyzed alkyne-nitrone cycloaddition involving rearrangement (CuANCR) with rate accelerations made possible by the use of surfactant micelles. We have investigated the factors that accelerate the aqueous CuANCR reaction and demonstrate enhanced modification of a model membrane-associated peptide. We discovered that lipids/surfactants and alkyne structure have a significant impact on the reaction rate, with biological lipids and electron-poor alkynes showing greater reactivity. These new findings have implications for the use of CuANCR for modifying integral membrane proteins as well as live cell labelling and other bioorthogonal applications.
The powerful effect of N-aryl substitution in promoting the thermal rearrangement of 5-spirocyclopropaneisoxazolidines
Cordero, Franca M.,Barile, Ingrid,De Sarlo, Francesco,Brandi, Alberto
, p. 6657 - 6660 (2007/10/03)
N-Alkyl 5-spirocyclopropaneisoxazolidines rearrange to tetrahydropyridone derivatives by heating. The presence of a phenyl ring on the nitrogen atom significantly reduces the rearrangement temperature. This effect is enhanced by electron-donating substituents and reduced by electron- withdrawing substituents on the phenyl ring.
