PLGA-PEG-supported Pd Nanoparticles as Efficient Catalysts for Suzuki-Miyaura Coupling Reactions in Water

Chimia (Aarau). 2016;70(4):252-7. doi: 10.2533/chimia.2016.252.

Abstract

Chemical transformations that can be performed selectively under physiological conditions are highly desirable tools to track biomolecules and manipulate complex biological processes. Here, we report a new nanocatalyst consisting of small palladium nanoparticles stabilized on the surface of PLGA-PEG nanoparticles that show excellent catalytic activity for the modification of biological building blocks through Suzuki-Miyaura cross-coupling reactions in water. Brominated or iodinated amino acids were coupled with aryl boronic acids in phosphate buffer in good yields. Interestingly, up to 98% conversion into the coupled amino acid could be achieved in 2 h at 37 °C using the stable, water-soluble cyclic triolborate as organometallic partner in the presence of only 1 mol% of palladium. These results pave the way for the modification of biomolecules in complex biological systems such as the intracellular space.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Boronic Acids / chemistry*
  • Catalysis
  • Halogenation
  • Hydrogen-Ion Concentration
  • Lactic Acid / chemistry*
  • Nanoparticles / chemistry*
  • Palladium / chemistry*
  • Polyglycolic Acid / chemistry*
  • Polylactic Acid-Polyglycolic Acid Copolymer
  • Water / chemistry

Substances

  • Amino Acids
  • Boronic Acids
  • Water
  • Polylactic Acid-Polyglycolic Acid Copolymer
  • Polyglycolic Acid
  • Lactic Acid
  • Palladium
  • benzeneboronic acid