Hexafluoroacetone as a Protecting and Activating Reagent: Synthesis of New Types of Fluoro-Substituted α-Amino, α-Hydroxy and α-Mercapto Acids

Abstract

Starting from (S)-aspartic, (S)-malic, (S)-citramalic and (S,R)-thiomalic acid, new types of 4,4-difluoro-substituted α-amino-, α-hydroxy- and α-mercaptopentanoic acids have been synthesized, applying hexafluoroacetone as protecting and activating reagent. The new partially fluorinated α-functionalized carboxylic acids represent interesting monomers for peptide and depsipeptide modification and for rational design and elucidation of secondary structure.

amino acids - hydroxy acids - mercapto acids - fluorine - peptides

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