Ephedrine-based diselenide: a promiscuous catalyst suitable to mimic the enzyme glutathione peroxidase (GPx) and to promote enantioselective C-C coupling reactions

Org Biomol Chem. 2012 Aug 28;10(32):6595-9. doi: 10.1039/c2ob25539a. Epub 2012 Jul 17.

Abstract

The ephedrine-based diselenide appears as a new promiscuous catalyst, able to generate optically active alcohols by addition of organozinc to aldehydes (up to 97% ee), and shows powerful GPx like activity, reducing H(2)O(2) to water in only 16.33 min (eleven times faster than PhSeSePh).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Drug Design
  • Ephedrine / chemistry*
  • Glutathione Peroxidase / chemistry*
  • Glutathione Peroxidase / metabolism
  • Molecular Mimicry*
  • Organoselenium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Organoselenium Compounds
  • Glutathione Peroxidase
  • Ephedrine