A Highly Active Biohybrid Catalyst for Olefin Metathesis in Water: Impact of a Hydrophobic Cavity in a β-Barrel Protein
ACS Catalysis2015Vol. 5(12), pp. 7519–7522
Citations Over TimeTop 10% of 2015 papers
Daniel F. Sauer, Tomoki Himiyama, Kengo Tachikawa, Kazuki Fukumoto, Akira Onoda, Eiichi Mizohata, Tsuyoshi Inoue, Marco Bocola, Ulrich Schwaneberg, Takashi Hayashi, Jun Okuda
Abstract
A series of Grubbs–Hoveyda type catalyst precursors for olefin metathesis containing a maleimide moiety in the backbone of the NHC ligand was covalently incorporated in the cavity of the β-barrel protein nitrobindin. By using two protein mutants with different cavity sizes and choosing the suitable spacer length, an artificial metalloenzyme for olefin metathesis reactions in water in the absence of any organic cosolvents was obtained. High efficiencies reaching TON > 9000 in the ROMP of a water-soluble 7-oxanorbornene derivative and TON > 100 in ring-closing metathesis (RCM) of 4,4-bis(hydroxymethyl)-1,6-heptadiene in water under relatively mild conditions (pH 6, T = 25–40 °C) were observed.
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