6162-49-8Relevant academic research and scientific papers
Phosphine-Mediated Bioconjugation of the 3′-End of RNA
Kitoun, Camélia,Fonvielle, Matthieu,Sakkas, Nicolas,Lefresne, Manon,Djago, Fabiola,Blancart Remaury, Quentin,Poinot, Pauline,Arthur, Michel,Etheve-Quelquejeu, Mélanie,Iannazzo, Laura
, p. 8034 - 8038 (2020/11/02)
Staudinger ligation is an attractive bio-orthogonal reaction that has been widely used to tag proteins, carbohydrates, and nucleic acids. Here, we explore the traceless variant of the Staudinger ligation for 3′-end modification of oligoribonucleotides. An azido-containing dinucleotide was used to study the ligation. Nine phosphines containing reactive groups, affinity purification tags, or photoswitch probes have been successfully obtained. The corresponding modified dinucleotides were synthesized and characterized by LC/MS. Mechanistic interpretations of the reaction are proposed, in particular, the unprecedented formation of an oxazaphospholane nucleotide derivative, which was favored by the vicinal position of 2′-N3 and 3′-OH functional groups on the terminal ribose has been observed. The post-functionalization of a 24-nt RNA with a photoactivable tag is also reported.
Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes
Riomet, Margaux,Decuypere, Elodie,Porte, Karine,Bernard, Sabrina,Plougastel, Lucie,Kolodych, Sergii,Audisio, Davide,Taran, Frédéric
, p. 8535 - 8541 (2018/05/30)
Emerging applications in the field of chemical biology are currently limited by the lack of bioorthogonal reactions allowing both removal and linkage of chemical entities on complex biomolecules. We recently discovered a novel reaction between iminosydnones and strained alkynes leading to two products resulting from ligation and fragmentation of iminosydnones under physiological conditions. We now report the synthesis of a panel of substituted iminosydnones and the structure reactivity relationship between these compounds and strained alkyne partners. This study identified the most relevant substituents, which allow to increase the rate of the transformation and to develop a bifunctional cleavable linker with improved kinetics.
Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes
Bernard, Sabrina,Audisio, Davide,Riomet, Margaux,Bregant, Sarah,Sallustrau, Antoine,Plougastel, Lucie,Decuypere, Elodie,Gabillet, Sandra,Kumar, Ramar Arun,Elyian, Jijy,Trinh, Minh Nguyet,Koniev, Oleksandr,Wagner, Alain,Kolodych, Sergii,Taran, Frédéric
, p. 15612 - 15616 (2017/12/02)
We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.
An efficient, one-pot synthesis of 3-alkyl or aryl sydnoneimines
Beal,Turnbull
, p. 673 - 676 (2007/10/02)
In a 'one-pot' process, a variety of 3-alkyl and 3-aryl sydnoneimine hydrochlorides can be prepared in high yield, under mild conditions, by nitrosation of the corresponding aminoacetonitrile with isoamyl nitrite in diethyl ether followed by cyclization w
