Reactivity of Biarylazacyclooctynones in Copper-Free Click Chemistry
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چکیده
منابع مشابه
Reactivity of Biarylazacyclooctynones in Copper-Free Click Chemistry
The 1,3-dipolar cycloaddition of cyclooctynes with azides, also called "copper-free click chemistry", is a bioorthogonal reaction with widespread applications in biological discovery. The kinetics of this reaction are of paramount importance for studies of dynamic processes, particularly in living subjects. Here we performed a systematic analysis of the effects of strain and electronics on the ...
متن کاملRearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry.
Highly strained biarylazacyclooctynone (BARAC) and analogous bioconjugation reagents were shown to undergo novel rearrangement and addition reactions leading to tetracyclic products. This may limit their practical applicability as bioorthogonal reporters for imaging biomolecules within living systems.
متن کاملRapid Cu-Free Click Chemistry with Readily Synthesized Biarylazacyclooctynones
Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. The reaction of azides with strained alkynes, such as cyclooctynes, readily forms a triazole product without the need for a toxic catalyst. Here we describe a biarylazacyclooctynone (BARAC) that has excepti...
متن کاملCopper-free click chemistry in living animals.
Chemical reactions that enable selective biomolecule labeling in living organisms offer a means to probe biological processes in vivo. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed for direct covalent modification of biomolecules with probes in the mouse, an important model organis...
متن کاملThiacycloalkynes for Copper-Free Click Chemistry**
Bioorthogonal chemistry enables the interrogation of biomolecules and physiological processes that are inaccessible by using conventional research tools. A common experimental protocol starts by labeling a target biomolecule in cells or live organisms with a bioorthogonal functional group. Then, a probe molecule bearing complementary functionality is added to the system and the ensuing bioortho...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2012
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja3000936