1253203-72-3Relevant academic research and scientific papers
Water-soluble, stable and azide-reactive strained dialkynes for biocompatible double strain-promoted click chemistry
Sharma, Krishna,Strizhak, Alexander V.,Fowler, Elaine,Wang, Xuelu,Xu, Wenshu,Hatt Jensen, Claus,Wu, Yuteng,Sore, Hannah F.,Lau, Yu Heng,Hyv?nen, Marko,Itzhaki, Laura S.,Spring, David R.
supporting information, p. 8014 - 8018 (2019/09/06)
The Sondheimer dialkyne is extensively used in double strain-promoted azide-alkyne cycloadditions. This reagent suffers with poor water-solubility and rapidly decomposes in aqueous solutions. This intrinsically limits its application in biological systems, and no effective solutions are currently available. Herein, we report the development of novel highly water-soluble, stable, and azide-reactive strained dialkyne reagents. To demonstrate their extensive utility, we applied our novel dialkynes to a double strain-promoted macrocyclisation strategy to generate functionalised p53-based stapled peptides for inhibiting the oncogenic p53-MDM2 interaction. These functionalised stapled peptides bind MDM2 with low nanomolar affinity and show p53 activation in a cellular environment. Overall, our highly soluble, stable and azide-reactive dialkynes offer significant advantages over the currently used Sondheimer dialkyne, and could be utilised for numerous biological applications.
Effect of resonance on the clickability of alkenyl azides in the strain-promoted cycloaddition with dibenzo-fused cyclooctynes
Yoshida, Suguru,Goto, Sayuri,Nishiyama, Yoshitake,Hazama, Yuki,Kondo, Masakazu,Matsushita, Takeshi,Hosoya, Takamitsu
supporting information, p. 1038 - 1041 (2019/08/21)
The clickabilities of various alkenyl and alkyl azides in the strain-promoted cycloaddition with dibenzo-fused cyclooctynes were investigated. Although alkenyl azides generally exhibited lower clickabilities than those of alkyl azides, a sterically-hindered alkenyl azide showed high reactivity comparable with those of alkyl azides. Theoretical analyses indicated that these unique reactivities are derived from the frontier molecular orbital interactions and distortability of the azido groups.
Substituted 5,6,11,12-tetradehydrodibenzo[ a, e ]cyclooctenes: Syntheses, properties, and DFT studies of substituted sondheimer-wong diynes
Xu, Feng,Peng, Lifen,Shinohara, Kenta,Morita, Takamoto,Yoshida, Suguru,Hosoya, Takamitsu,Orita, Akihiro,Otera, Junzo
, p. 11592 - 11608 (2015/01/09)
Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer-Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner by isolation of the heterocoupled vinyl sulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammograms of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reactions and nucleophilic and electrophilic additions.
CYCLIC COMPOUND, METHOD FOR PRODUCING CYCLIC COMPOUND, AND METHOD FOR MODIFYING BIOLOGICAL MOLECULE
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Paragraph 0115-0124; 0399-0402, (2013/03/26)
The invention aims in establishing a method for modifying biomolecules using a reaction that efficiently modifies biomolecules and is widely applicable. The invention thus provides a cyclic compound containing two triazole rings formed by adding and ligating an azide compound possessing an azido group to each of the two carbon-carbon triple bond sites of an eight-membered cyclic skeleton of a cyclic diyne compound by a double click reaction; a method for producing a cyclic compound using a double click reaction; and a method for modifying biomolecules.
