1345667-96-0Relevant academic research and scientific papers
Exploring isonitrile-based click chemistry for ligation with biomolecules
Stoeckmann, Henning,Neves, Andre A.,Stairs, Shaun,Brindle, Kevin M.,Leeper, Finian J.
, p. 7303 - 7305 (2011)
We show here that isonitriles can perform click reactions with tetrazines in aqueous media, making them promising candidates for ligation reactions in chemical biology and polymer chemistry. This is the first time that a [4+1] cycloaddition has been used as a biocompatible ligation reaction.
A genetically encoded isonitrile lysine for orthogonal bioorthogonal labeling schemes
Biró, Adrienn,Cserép, Gergely B.,Kele, Péter,Molnár, Tibor á.,Németh, Krisztina,S?veges, Bianka,Szabó, Edit,Szatmári, ágnes,Várady, Gy?rgy
supporting information, (2021/08/26)
Bioorthogonal click-reactions represent ideal means for labeling biomolecules selectively and specifically with suitable small synthetic dyes. Genetic code expansion (GCE) technology enables efficient site-selective installation of bioorthogonal handles o
Stable, Reactive, and Orthogonal Tetrazines: Dispersion Forces Promote the Cycloaddition with Isonitriles
Tu, Julian,Svatunek, Dennis,Parvez, Saba,Liu, Albert C.,Levandowski, Brian J.,Eckvahl, Hannah J.,Peterson, Randall T.,Houk, Kendall N.,Franzini, Raphael M.
supporting information, p. 9043 - 9048 (2019/06/24)
The isocyano group is a structurally compact bioorthogonal functional group that reacts with tetrazines under physiological conditions. Now it is shown that bulky tetrazine substituents accelerate this cycloaddition. Computational studies suggest that dispersion forces between the isocyano group and the tetrazine substituents in the transition state contribute to the atypical structure–activity relationship. Stable asymmetric tetrazines that react with isonitriles at rate constants as high as 57 L mol?1 s?1 were accessible by combining bulky and electron-withdrawing substituents. Sterically encumbered tetrazines react selectively with isonitriles in the presence of strained alkenes/alkynes, which allows for the orthogonal labeling of three proteins. The established principles will open new opportunities for developing tetrazine reactants with improved characteristics for diverse labeling and release applications with isonitriles.
