Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 + 2] cycloaddition ("click") reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethyn...

The reaction pathway for the addition of alkynes to tetramesityldigermene was examined using a cyclopropyl alkyne mechanistic probe. The results obtained indicate that the reaction is stepwise and involves biradical intermediates.

Alkyne metathesis is increasingly explored as a reliable method to close macrocyclic rings, but there are no prior examples of an alkyne-metathesis-based homodimerization approach to natural products. In this approach to the cytotoxic C2-symmetric marine-derived bis(lactone) disorazole C1, a highly convergent, modular strategy is employed featuring cyclization through an ambitious one-pot alkyn...

The copper-catalyzed azide alkyne cycloaddition is employed to modify phosphatidylcholine precursors with sn-2 acyl chains containing terminal alkyne or azide groups. Although the reactions are conducted as biphasic dispersions, the yields are essentially quantitative. Bolaamphiphiles are formed by simply clicking together two phosphatidylcholine alkyne precursors to a central bisazide scaffold...

We report an assay for determining the number of fluorophores conjugated to single plasmid DNA molecules and apply this to compare the efficiency of fluorophore coupling strategies for covalent DNA labelling. We compare a copper-catalyzed azide-alkyne cycloaddition reaction, amine to N-hydroxysuccinimidyl ester coupling reaction and strain-promoted azide-alkyne cycloaddition reaction for fluore...

Radical-mediated thiol-yne step-growth photopolymerizations are utilized to form highly cross-linked polymer networks. This reaction mechanism is shown to be analogous to the thiol-ene photopolymerization; however, each alkyne functional group is capable of consecutive reaction with two thiol functional groups. The thiol-yne reaction involves the sequential propagation of a thiyl radical with e...

A synthetic approach to the modification of drug Riluzole with pharmacologically active fragments (adamantane, carbazole, tetrahydrocarbazole, γ-carboline, and phenothiazine) was proposed, which is based on copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition azide-containing pharmacophores alkyne-containing derivatives Riluzole.

This article is available online at http://www.jlr.org to radioactive labeling. They are convenient and sensitive reporters, but in general contain spacious tags of high impact on the structure, likely to infl uence specifi city and kinetic parameters of enzymatic reactions. Although there are reports of assays with unchanged affi nity of the enzyme to fl uorescently labeled substrates, notably...