Supramolecular Anchoring of NCN-Pincer Palladium Complexes into a β-Barrel Protein Host: Molecular-Docking and Reactivity Insights

Abstract : Several prochiral NCN pincer complexes of palladium(II) including hemilabile ligands and a long aliphatic chain were synthesized and characterized spectroscopically. In some of the complexes, the presence of two different substituents on the N donor atoms made them stereogenic so that they were isolated as a mixture of diastereoisomers, which could be differentiated by 1 H NMR. Binding of some of these complexes to bovine b-lactoglobin by insertion within its inner cavity was theoretically investigated by molecular docking simulations and experimentally confirmed by CD spectroscopy. Adjunction of H-bond donor substituents on the ligand framework gave more stable supramolecular protein – complex assemblies. These constructs were shown to catalyze aldol condensation reactions in aqueous medium affording in some cases the less favorable cis-product. Since the corresponding complexes gave exclusively the trans product in the absence of b-lactoglobulin, this unusual diastereoselectivity was ensued by the second sphere of coordination brought by the protein host.
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Lucrèce Pocquet, Nikolay Vologdin, Giuseppe Felice Mangiatordi, Ilaria Ciofini, Orazio Nicolotti, et al.. Supramolecular Anchoring of NCN-Pincer Palladium Complexes into a β-Barrel Protein Host: Molecular-Docking and Reactivity Insights. European Journal of Inorganic Chemistry, Wiley-VCH Verlag, 2017, 2017 (30), pp.3622-3634. ⟨10.1002/ejic.201700365⟩. ⟨hal-01585231⟩

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