Second-generation artificial hydrogenases based on the biotin–avidin technology: Improving selectivity and organic solvent tolerance by introduction of an (R)-proline spacer |
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Institution: | Institute of Chemistry, University of Neuchâtel, av. Bellevaux, 51, CP 158, CH 2009 Neuchâtel, Switzerland |
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Abstract: | We report on our efforts to create efficient artificial metalloenzymes for the enantioselective hydrogenation of N-protected dehydroamino acids using streptavidin as host protein. Introduction of an (R)-proline spacer between the biotin anchor and the diphosphine moiety affords a versatile ligand Biot-(R)-Pro-1 which displays good (S)-selectivities in the presence of streptavidin (91% ee). The resulting artificial metalloenzyme Rh(Biot-(R)-Pro-1)(COD)]+ ⊂ WT-Sav displays increased stability against organic solvents. |
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