4785-56-2Relevant articles and documents
Cell-Trappable BODIPY-NBD Dyad for Imaging of Basal and Stress-Induced H2S in Live Biosystems
Huang, Haojie,Ji, Xiuru,Jiao, Yan,Pang, Zhili,Sun, Lu,Tang, Xinjing,Tu, Xiaoqiang,Xi, Zhen,Ye, Haishun,Yi, Long
, p. 1733 - 1741 (2022/02/05)
H2S is a gaseous signaling molecule that is involved in many physiological and pathological processes. In general, the level of intracellular H2S (1 μM) is much lower than that of GSH (~1–10 mM), leading to the remaining challenge o
Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates
Li, Jian-Jun,Wang, Cheng-Gang,Yu, Jin-Feng,Wang, Peng,Wang, Peng,Yu, Jin-Quan
, p. 4692 - 4696 (2020/06/25)
An efficient Cu-catalyzed C-H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C-H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product from the internal vinyl borons will lead to installation of secondary alkyls.
Sterically Shielded, Stabilized Nitrile Imine for Rapid Bioorthogonal Protein Labeling in Live Cells
An, Peng,Lewandowski, Tracey M.,Erbay, Tug?e G.,Liu, Peng,Lin, Qing
, p. 4860 - 4868 (2018/04/16)
In pursuit of fast bioorthogonal reactions, reactive moieties have been increasingly employed for selective labeling of biomolecules in living systems, posing a challenge in attaining reactivity without sacrificing selectivity. To address this challenge, here we report a bioinspired strategy in which molecular shape controls the selectivity of a transient, highly reactive nitrile imine dipole. By tuning the shape of structural pendants attached to the ortho position of the N-aryl ring of diaryltetrazoles-precursors of nitrile imines, we discovered a sterically shielded nitrile imine that favors the 1,3-dipolar cycloaddition over the competing nucleophilic addition. The photogenerated nitrile imine exhibits an extraordinarily long half-life of 102 s in aqueous medium, owing to its unique molecular shape that hinders the approach of a nucleophile as shown by DFT calculations. The utility of this sterically shielded nitrile imine in rapid (~1 min) bioorthogonal labeling of glucagon receptor in live mammalian cells was demonstrated.