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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Progress towards bioorthogonal catalysis with organometallic compounds.

Timo Völker1, Felix Dempwolff, Peter L Graumann

  • 1Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35043 Marburg (Germany).

Angewandte Chemie (International Ed. in English)
|August 21, 2014
PubMed
Summary

New ruthenium catalysts enable bioorthogonal reactions in living cells. These catalysts efficiently uncage amines and activate drugs, showing great promise for chemical biology and medicinal chemistry applications.

Keywords:
bioorthogonalityhomogeneous catalysisprodrugsuncaging

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Area of Science:

  • Organometallic Chemistry
  • Chemical Biology
  • Medicinal Chemistry

Background:

  • Bioorthogonal catalysis within living systems presents significant challenges.
  • Potential applications in chemical biology and medicinal chemistry are vast.
  • Developing efficient catalysts for in vivo transformations is crucial.

Purpose of the Study:

  • To develop highly active organometallic ruthenium complexes for bioorthogonal catalysis.
  • To demonstrate catalytic activity under biologically relevant conditions, including within living cells.
  • To showcase applications in uncaging amines and activating drugs in situ.

Main Methods:

  • Synthesis and characterization of novel organometallic ruthenium complexes.
  • Testing catalytic activity in aqueous media with air and thiols.
  • Live-cell imaging using caged fluorescent probes in HeLa cells.
  • In-cell drug activation assays to induce apoptosis.

Main Results:

  • Ruthenium catalysts achieved high turnover numbers (up to 270 cycles) for uncaging allyl carbamate protected amines.
  • Catalysts demonstrated activity in the presence of water, air, and millimolar thiol concentrations.
  • Live-cell imaging confirmed rapid fluorescence development in the cytoplasm, supporting bioorthogonality.
  • Catalytic in-cell activation of a caged anticancer drug successfully induced apoptosis in HeLa cells.

Conclusions:

  • Organometallic ruthenium complexes are effective catalysts for bioorthogonal transformations in living cells.
  • These catalysts offer a powerful tool for applications in chemical biology and drug delivery.
  • The developed system enables precise control over molecular activation within cellular environments.