Synthesis of taurine-containing peptides, sulfonopeptides, and N- and O-conjugates

J Org Chem. 2014 Mar 21;79(6):2688-93. doi: 10.1021/jo500181g. Epub 2014 Mar 11.

Abstract

Taurine-containing water-soluble peptidomimetics were designed and synthesized. N-terminal taurine acylations allowed synthesis of a number of taurine-containing peptides. N-protection of taurine with Cbz and SO2-activation with benzotriazole followed by coupling with various amino esters, dipeptides and nucleophiles provided taurine N- and O-conjugates and sulfonopeptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Nitrogen / chemistry*
  • Oxygen / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Peptidomimetics / chemistry*
  • Sulfhydryl Compounds / chemistry*
  • Taurine / chemical synthesis*
  • Taurine / chemistry
  • Triazoles / chemistry*

Substances

  • Peptides
  • Peptidomimetics
  • Sulfhydryl Compounds
  • Triazoles
  • Taurine
  • benzotriazole
  • Nitrogen
  • Oxygen