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Université de Neuchâtel

(Strept)avidin as Host for Biotinylated Coordination Complexes: Stability, Chiral Discrimination, and Cooperativity

Loosli, Andreas ; Rusbandi, Untung Edy ; Gradinaru, Julieta ; Bernauer, Klaus ; Schlaepfer, Carl Wilhelm ; Meyer, Michel ; Mazurek, Sylwester ; Novic, Marjana ; Ward, Thomas R.

In: Inorganic Chemistry, 2006, vol. 45, no. 2, p. 660-668

To determine the stepwise association constants, to assess cooperativity and chiral discrimination properties of (strept)avidin toward biotinylated coordination complexes, diastereopure [Ru(bpy)2(Biot-bpy)]2+ (1) complexes were synthesized. Analysis of the CD titration data suggests a strong cooperativity between the first and the second binding events in tetrameric...

Université de Neuchâtel

Artificial Metalloenzymes: (Strept)avidin as Host for Enantioselective Hydrogenation by Achiral Biotinylated Rhodium−Diphosphine Complexes

Skander, Myriem ; Humbert, Nicolas ; Collot, Jérôme ; Gradinaru, Julieta ; Klein, Gérard ; Loosli, Andreas ; Sauser, Jérôme ; Zocchi, Andrea ; Gilardoni, François ; Ward, Thomas R.

In: Journal of the American Chemical Society (JACS), 2004, vol. 126, no. 44, p. 14411–14418

We report on the generation of artificial metalloenzymes based on the noncovalent incorporation of biotinylated rhodium−diphosphine complexes in (strept)avidin as host proteins. A chemogenetic optimization procedure allows one to optimize the enantioselectivity for the reduction of acetamidoacrylic acid (up to 96% ee (R) in streptavidin S112G and up to 80% ee (S) in WT avidin)....

Université de Neuchâtel

Artificial Metalloenzymes for Enantioselective Catalysis Based on Biotin−Avidin

Collot, Jérôme ; Gradinaru, Julieta ; Humbert, Nicolas ; Skander, Myriem ; Zocchi, Andrea ; Ward, Thomas R.

In: Journal of the American Chemical Society (JACS), 2003, vol. 125, no. 30, p. 9030-9031

Incorporation of biotinylated racemic three-legged d6-piano stool complexes in streptavidin yields enantioselective transfer hydrogenation artificial metalloenzymes for the reduction of ketones. Having identified the most promising organometallic catalyst precursors in the presence of wild-type streptavidin, fine-tuning of the selectivity is achieved by saturation mutagenesis at...

Université de Neuchâtel

Artificial Transfer Hydrogenases Based on the Biotin−(Strept)avidin Technology: Fine Tuning the Selectivity by Saturation Mutagenesis of the Host Protein

Letondor, Christophe ; Pordea, Anca ; Humbert, Nicolas ; Ivanova, Anita ; Mazurek, Sylwester ; Novic, Marjana ; Ward, Thomas R.

In: Journal of the American Chemical Society (JACS), 2006, vol. 128, no. 25, p. 8320-8328

Incorporation of biotinylated racemic three-legged d6-piano stool complexes in streptavidin yields enantioselective transfer hydrogenation artificial metalloenzymes for the reduction of ketones. Having identified the most promising organometallic catalyst precursors in the presence of wild-type streptavidin, fine-tuning of the selectivity is achieved by saturation mutagenesis at...

Université de Fribourg

(Strept)avidin as host for biotinylated coordination complexes: stability, chiral discrimination, and cooperativity

Loosli, Andreas ; Rusbandi, Untung Edy ; Gradinaru, Julieta ; Bernauer, Klaus ; Schlaepfer, Carl Wilhelm ; Meyer, Michel ; Mazurek, Sylwester ; Novic, Marjana ; Ward, Thomas R.

In: Inorganic Chemistry, 2006, vol. 45, no. 2, p. 660 -668

Incorporation of a biotinylated ruthenium tris(bipyridine) [Ru(bpy)₂(Biot-bpy)]²⁺ (1) in either avidin or streptavidin-(strept)avidin-can be conveniently followed by circular dichroism spectroscopy. To determine the stepwise association constants, cooperativity, and chiral discrimination properties, diastereopure (Λ and δ)-1 species were synthesized and incorporated in...

Université de Neuchâtel

Hierarchical Self-Assembly of One-Dimensional Streptavidin Bundles as a Collagen Mimetic for the Biomineralization of Calcite

Burazerovic, Sabina ; Gradinaru, Julieta ; Pierron, Julien ; Ward, Thomas R.

In: Angewandte Chemie International Edition, 2007, vol. 46, no. 29, p. 5510-5514

We report on our efforts to create efficient artificial metalloenzymes for the enantioselective hydrogenation of N-protected dehydroamino acids using either avidin or streptavidin as host proteins. Introduction of chiral amino acid spacers - phenylalanine or proline - between the biotin anchor and the flexible aminodiphosphine moiety 1, combined with saturation mutagenesis at...

Université de Neuchâtel

Second Generation Artificial Hydrogenases Based on the Biotin-Avidin Technology: Improving Activity, Stability and Selectivity by Introduction of Enantiopure Amino Acid Spacers

Rusbandi, Untung E. ; Lo, Cheikh ; Skander, Myriem ; Ivanova, Anita ; Creus, Marc ; Humbert, Nicolas ; Ward, Thomas R.

In: Advanced Synthesis & Catalysis, 2007, vol. 349, no. 11-12, p. 1923-1930

We report on our efforts to create efficient artificial metalloenzymes for the enantioselective hydrogenation of N-protected dehydroamino acids using either avidin or streptavidin as host proteins. Introduction of chiral amino acid spacers - phenylalanine or proline - between the biotin anchor and the flexible aminodiphosphine moiety 1, combined with saturation mutagenesis at...

Université de Neuchâtel

Second-generation artificial hydrogenases based on the biotin–avidin technology: Improving selectivity and organic solvent tolerance by introduction of an (R)-proline spacer

Rusbandi, Untung E. ; Skander, Myriem ; Ivanova, Anita ; Malan, Christophe ; Ward, Thomas R.

In: Comptes Rendus Chimie, 2007, vol. 10, no. 8, p. 678-683

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...

Université de Neuchâtel

Designed evolution of artificial metalloenzymes: protein catalysts made to order

Creus, Marc ; Ward, Thomas R.

In: Organic & Biomolecular Chemistry, 2007, vol. 5, no. 12, p. 1835-1844

Artificial metalloenzymes based on biotin–streptavidin technology, a fusion of chemistry and biology, illustrate how asymmetric catalysts can be improved and evolved using chemogenetic approaches.