Synthesis of N-quinonyltaurines

Amino Acids. 2003 Apr;24(3):281-7. doi: 10.1007/s00726-002-0407-4.

Abstract

Both 1,4-benzoquinones and 1,4-naphthoquinones were attached to the non-proteinogenic amino acid taurine to form N-quinonyl taurine derivatives. The products were formed via the direct Michael-like addition or by substitution of a good leaving group. An attempt to bridge the two moieties via an ureido spacer resulted in the formation of a bis-quinonylamino isocyanurate derivative. Preliminary MO calculations provided internal ground-state geometries and orbital coefficients of the HOMO levels in two representing taurine conjugates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoquinones / chemistry
  • Models, Chemical
  • Models, Molecular
  • Molecular Structure
  • Naphthoquinones / chemistry
  • Quinones / chemistry*
  • Taurine / chemical synthesis*
  • Taurine / chemistry

Substances

  • Benzoquinones
  • Naphthoquinones
  • Quinones
  • Taurine
  • 1,4-naphthoquinone