Abstract
As a powerful tool for chemical biology, bioorthogonal chemistry broadens the ways to explore the mystery of life. In this field, transition metal catalysts (TMCs) have received much attention because TMCs can rapidly catalyze chemical transformations that cannot be accomplished by bio-enzymes. However, fine controlling chemical reactions in living systems like bio-enzymes is still a great challenge. Herein, we construct a versatile light-controlled bioorthogonal catalyst by modifying macroporous silica-Pd0 with supramolecular complex of azobenzene (Azo) and β-cyclodextrin (CD). Its catalytic activity can be regulated by light-induced structural changes, mimicking allosteric regulation mechanism of bio-enzymes. The light-gated heterogeneous TMCs are important for in situ controlling bioorthogonal reactions and have been successfully used to synthesize a fluorescent probe for cell imaging and mitochondria-specific targeting agent by Suzuki–Miyaura cross-coupling reaction. Endowing the bioorthogonal catalyst with new functions is highly valuable for realizing more complex researches in biochemistry.
Highlights
As a powerful tool for chemical biology, bioorthogonal chemistry broadens the ways to explore the mystery of life
There are three major advantages of our designed catalysts: (1) the synthetic method of the heterogeneous transition metal catalysts (TMCs) is versatile and easy to be applied for constructing different kinds of catalysts, such as Pt, Ru, Rh, and so on. (2) The reversible interaction between Azo and CD endows the bioorthogonal catalyst with well reversibility, providing a great promise for broadening potential application of bioorthogonal catalysts in biosystem
The heterogeneous nanocatalysts were recyclable with high catalytic activity (Supplementary Table 3). These results suggested that the light-gated transition metal catalysts had good spatial and temporal resolution
Summary
As a powerful tool for chemical biology, bioorthogonal chemistry broadens the ways to explore the mystery of life. Cucurbit[7]uril has been used to block the access to the catalytic site of Ru or Pd catalysts on the surface of Au nanoparticles, and the catalyst can be re-activated by extra addition of 1-adamantylamine (ADA)[25] This is an innovative design for TMC-mediated bioorthogonal chemistry. We demonstrate that the designed heterogeneous catalyst could effectively mediate the bioorthogonal reactions in situ through light Such light-gated control of bioorthogonal catalysis in living cells has not been demonstrated to date this issue is important for activating catalytic process at target locations and artificially changing catalytic activity to maintain homeostasis for long-term therapeutics
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