An efficient and cost-effective Mn(I)-catalyzed site-selective C-H activation of 2-arylpyridines with maleimides has been described. This approach facilitates the synthesis of 3-arylated succinimide derivatives with high site selectivity, chemoselectivity, catalytic efficiency, and outstanding tolerance to numerous functional groups. The practicality of this approach is further evidenced by its successful application in large-scale reactions and the conversion of the synthesized succinimide derivatives into other valuable compounds.
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http://dx.doi.org/10.1021/acs.joc.4c01737 | DOI Listing |
Metabolites
December 2024
Graduate Institute of Biomedical Sciences, China Medical University, Taichung 40402, Taiwan.
Covalent modification of proteins at specific, predetermined sites is essential for advancing biological and biopharmaceutical applications. Site-selective labeling techniques for protein modification allow us to effectively track biological function, intracellular dynamics, and localization. Despite numerous reports on modifying target proteins with functional chemical probes, unique organic reactions that achieve site-selective integration without compromising native functional properties remain a significant challenge.
View Article and Find Full Text PDFNew Phytol
December 2024
PFR, Chemistry Department, University of Otago, Dunedin, 9016, New Zealand.
The potential of cannabinoids to address public health challenges has stimulated exploration into alternative sources and production technologies. Radula marginata, an endemic Aotearoa/New Zealand liverwort, produces the bibenzyl cannabinoid perrottetinene (PET), analogous to Cannabis psychoactive tetrahydrocannabinol (THC). Structural differences between PET and THC could alter therapeutic interactions and mitigate adverse side effects.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Institute for Molecular Bioscience, Australian Research Council Centre of Excellence for Innovations in Peptide and Protein Science, The University of Queensland, Brisbane, Queensland 4072, Australia.
Transpeptidases are specialized enzymes that have evolved for site-selective modification of peptides and proteins at their backbone termini. Approaches for adapting transpeptidases to catalyze side chain modifications are substantially more restricted, and typically rely on large recognition tags or require specific reaction conditions that are not easily compatible with broader applications. Here we show that the engineered asparaginyl ligase AEP1 catalyzes direct isopeptide ligation by accepting an internal 2,3-diaminopropionic acid (Dap) residue adjacent to Leu, a motif that mimics the canonical N-terminal Gly-Leu substrate.
View Article and Find Full Text PDFOrg Lett
December 2024
School of Pharmacy, Hebei Medical University, Shijiazhuang 050017, China.
We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products.
View Article and Find Full Text PDFOrg Lett
December 2024
College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao, 266042, China.
The site-selective functionalization of cyclic amides provides an attractive protocol for the synthesis of valuable molecules. We report herein an electrochemical desaturation and β-thiocyanation of cyclic amides under external oxidant-free conditions. This method exhibits broad functional group tolerance, excellent selectivity, mild reaction conditions and can be applied for late-stage functionalization of bioactive molecules.
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