A Carbodiimide-Fueled Reaction Cycle That Forms Transient 5(4 H )-Oxazolones.

Autor: Chen X; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany., Stasi M; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany., Rodon-Fores J; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany., Großmann PF; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany., Bergmann AM; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany., Dai K; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany., Tena-Solsona M; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany., Rieger B; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany., Boekhoven J; Department of Chemistry, School of Natural Sciences, Technical University of Munich, Lichtenbergstraße 4, 85748 Garching, Germany.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2023 Mar 29; Vol. 145 (12), pp. 6880-6887. Date of Electronic Publication: 2023 Mar 17.
DOI: 10.1021/jacs.3c00273
Abstrakt: In life, molecular architectures, like the cytoskeletal proteins or the nucleolus, catalyze the conversion of chemical fuels to perform their functions. For example, tubulin catalyzes the hydrolysis of GTP to form a dynamic cytoskeletal network. In contrast, myosin uses the energy obtained by catalyzing the hydrolysis of ATP to exert forces. Artificial examples of such beautiful architectures are scarce partly because synthetic chemically fueled reaction cycles are relatively rare. Here, we introduce a new chemical reaction cycle driven by the hydration of a carbodiimide. Unlike other carbodiimide-fueled reaction cycles, the proposed cycle forms a transient 5(4 H )-oxazolone. The reaction cycle is efficient in forming the transient product and is robust to operate under a wide range of fuel inputs, pH, and temperatures. The versatility of the precursors is vast, and we demonstrate several molecular designs that yield chemically fueled droplets, fibers, and crystals. We anticipate that the reaction cycle can offer a range of other assemblies and, due to its versatility, can also be incorporated into molecular motors and machines.
Databáze: MEDLINE