Pd(II) Complexes of Chiral Proline-Derived Ligands: Application for Dynamic Thermodynamic Resolution of α-Amino Acids and Their Antibacterial Activities

J Org Chem. 2023 Mar 17;88(6):3808-3821. doi: 10.1021/acs.joc.3c00008. Epub 2023 Mar 3.

Abstract

Novel type of Pd(II) complexes have been synthesized under operationally simple and convenient conditions and applied in the dynamic thermodynamic resolution of racemic N,C-unprotected α-amino acids. After rapid hydrolysis, these Pd(II) complexes produced the corresponding α-amino acids in satisfactory yields and enantioselectivities, accompanied by the recyclable proline-derived ligand. In addition, the method can be readily applied for S/R interconversion to obtain unnatural (R)-α-amino acids from readily available (S)-α-amino acids. Furthermore, biological assays showed that Pd(II) complexes (S,S)-3i and (S,S)-3m exhibited significant antibacterial activities similar to vancomycin, which may represent promising lead structures for further development of antibacterial agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids* / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Ligands
  • Proline* / chemistry
  • Stereoisomerism
  • Thermodynamics

Substances

  • Proline
  • Ligands
  • Amino Acids
  • Anti-Bacterial Agents