Intracellular Deprotection Reactions Mediated by Palladium Complexes Equipped with Designed Phosphine Ligands

被引:81
作者
Martinez-Calvo, Miguel
Couceiro, Jose R.
Destito, Paolo
Rodriguez, Jessica [2 ]
Mosquera, Jesus [3 ,4 ]
Mascarenas, Jose L. [1 ]
机构
[1] Univ Santiago Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Rua Jenaro de la Fuente S-N, Santiago De Compostela 15782, Spain
[2] Univ Paul Sabatier, Lab Heterochim Fondamentale & Appl, CNRS, UMR 5069, 118 Route Narbonne, F-31062 Toulouse 09, France
[3] CIC BiomaGUNE, Paseo Miramon 182, Donostia San Sebastian 20014, Spain
[4] Ciber BBN, Paseo Miramon 182, Donostia San Sebastian 20014, Spain
基金
欧洲研究理事会;
关键词
palladium; discrete complexes; bioorthogonal; intracellular catalysis; mitochondrial confinement; CROSS-COUPLING REACTIONS; LIVING CELLS; ARTIFICIAL METALLOENZYMES; ALLYLCARBAMATE CLEAVAGE; CATALYSIS; PROTEINS;
D O I
10.1021/acscatal.8b01606
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Discrete palladium(II) complexes featuring purposely designed phosphine ligands can promote depropargylation and deallylation reactions in cell lysates. These complexes perform better than other palladium sources, which apparently are rapidly deactivated in such hostile complex media. This good balance between reactivity and stability allows the use of these discrete phosphine palladium complexes in living mammalian cells, whereby they can mediate similar transformations. The presence of a phosphine ligand in the coordination sphere of palladium also provides for the introduction of targeting groups, such as hydrophobic phosphonium moieties, which facilitate the accumulation of the complexes in mitochondria.
引用
收藏
页码:6055 / 6061
页数:13
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