2468-56-6Relevant articles and documents
Radical reactions in organoboron chemistry II - Inter- and intramolecular addition of carbon centered radicals to alkenylboranes
Guennouni,Lhermitte,Cochard,Carboni
, p. 6999 - 7018 (1995)
The intermolecular addition of carbon centered radicals to alkenylboranes has been studied. The influence of the olefin and boron substituents on the reactivity and the regioselectivity was determined. Competitive experiments were carried out to estimate the relative reactivity of a series of vinylboranes and other electron deficient alkenes. Intramolecular versions of these additions were also described as well as some further transformations of selected adducts.
Site-specific fluorogenic protein labelling agent for bioconjugation
Keillor, Jeffrey W.,Lee, Ann C.,Racine, Karl é.,Tsao, Kelvin K.
, (2020)
Many clinically relevant therapeutic agents are formed from the conjugation of small molecules to biomolecules through conjugating linkers. In this study, two novel conjugating linkers were prepared, comprising a central coumarin core, functionalized with a dimaleimide moiety at one end and a terminal alkyne at the other. In our first design, we developed a protein labelling method that site-specifically introduces an alkyne functional group to a dicysteine target peptide tag that was genetically fused to a protein of interest. This method allows for the subsequent attachment of azide-functionalized cargo in the facile synthesis of novel protein-cargo conjugates. However, the fluorogenic aspect of the reaction between the linker and the target peptide was less than we desired. To address this shortcoming, a second linker reagent was prepared. This new design also allowed for the site-specific introduction of an alkyne functional group onto the target peptide, but in a highly fluorogenic and rapid manner. The site-specific addition of an alkyne group to a protein of interest was thus monitored in situ by fluorescence increase, prior to the attachment of azide-functionalized cargo. Finally, we also demonstrated that the cargo can also be attached first, in an azide/alkyne cycloaddition reaction, prior to fluorogenic conjugation with the target peptide-fused protein.
A click-based modular approach to introduction of peroxides onto molecules and nanostructures
Dussault, Patrick H.,Horn, Alissa
, p. 44408 - 44429 (2020/12/28)
Copper-promoted azide/alkyne cycloadditions (CuAAC) are explored as a tool for modular introduction of peroxides onto molecules and nanomaterials. Dialkyl peroxide-substituted alkynes undergo Cu(i)-promoted reaction with azides in either organic or biphas
Scalable and Phosphine-Free Conversion of Alcohols to Carbon-Heteroatom Bonds through the Blue Light-Promoted Iodination Reaction
Liu, Bin,Elder, W. Zachary,Miyake, Garret M.
, p. 3717 - 3727 (2020/03/04)
One of the fundamental and highly valuable transformations in organic chemistry is the nucleophilic substitution of alcohols. Traditionally, these reactions require strategies that employ stoichiometric hazardous reagents and are associated with difficulty in purification of the by-products. To overcome these challenges, here, we report a simple route toward the diverse conversion of alcohols via an SN2 pathway, in which blue light-promoted iodination is used to form alkyl iodide intermediates from simple unreactive alcohols. The scope of the process tolerates a range of nucleophiles to construct C-N, C-O, C-S, and C-C bonds. Furthermore, we also demonstrate that this method can be used for the preparation and late-stage functionalization of pharmaceuticals, as highlighted by the syntheses of thiocarlide, butoxycaine, and pramoxine.
