IBAAC · An integrated biomimetic approach to asymmetric catalysis

Final Activity Report Summary - IBAAC (An Integrated Biomimetic Approach to Asymmetric Catalysis)

New high-throughput screening methods based on immunoassay techniques were developed and used for the monitoring of asymmetric and cross-coupling reactions. Thousands of catalysts, such as organometallic, enzymatic or hybrid catalysts were screened thanks to the successful collaboration through the network and several interesting catalytic systems were highlighted for target reactions. Asymmetric catalysis, i.e. the production of handed molecules using a catalytic process, is widely implemented in many industrial processes. It is best performed with either homogeneous or enzymatic catalysts. Today, catalyst discovery and optimisation is a lengthy procedure which mostly relies on a trial-and-error approach. The ‘Integrated biomimetic approach to asymmetric catalysis’ (IBAAC) project aimed at creating hybrid catalysts with improved properties via the combination of an active organometallic moiety with a macromolecule, e.g. a protein, peptide-dendrimer, polymer etc. Hybrid catalyst production and optimisation was implemented and high-throughput quantification methods were developed for this purpose. Using this innovative approach, the IBAAC network developed several versatile enantioselective hybrid catalysts for hydrogenation, transfer hydrogenation, aldol, Diels-Alder, ester hydrolysis and sulfoxidation. During the four years of the project the ‘University of Bologna’ (UNIBO) explored new reactions, focussing our attention on the development of novel chiral ligands. We successfully prepared more than 30 new ligands and provided them to research teams in the IBAAC project. The ligands were used in high-throughput screening tests of new enantioselective reactions. In a joint project, some ligands were active for the addition of water to diazoacetate. In addition to this major goal, we explored the possibility of preparing new atropoisomeric ligands based on simply aromatic substitutions which were performed with indoles and pyrroles. With the participation of ‘Chemspeed Technologies’ as a premier provider for automated chemistry workflow solutions, we sought to gain new scientific collaborations and improve the technology for the (bio-)organic community. The outcome exceeded our expectations, as we not only improved our technology but also invented a new tool that allowed for further chemical treatment, while the collaborations between researchers remained active after the project completion. Computational methods were used to model two types of asymmetric catalysts and were based on the dendrimers and the streptavidin-biotin technology. The results indicated that the outcome of asymmetric catalysis in a protein environment was the interplay of delicate structural contributions. Useful structure and activity models and software tools were prepared. Finally, new structural descriptors were developed.

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