Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid - a CF3O-containing analogue of natural lipophilic amino acids

Org Biomol Chem. 2017 Jan 18;15(3):672-679. doi: 10.1039/c6ob02436j.

Abstract

2-Amino-2-(trifluoromethoxy)butanoic acid (O-trifluoromethyl homoserine) was synthesized as a racemate and in both enantiomeric forms. The measured pKa and log D values establish the compound as a promising analogue of natural aliphatic amino acids.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Butyrates / chemical synthesis*
  • Butyrates / chemistry*
  • Chemistry, Physical
  • Hydrocarbons, Fluorinated / chemistry*
  • Hydrophobic and Hydrophilic Interactions
  • Models, Molecular
  • Molecular Structure

Substances

  • 2-amino-4-(trifluoromethoxy)butanoic acid
  • Amino Acids
  • Butyrates
  • Hydrocarbons, Fluorinated