Convenient Conversion of Amino Acids to Their N-Hydroxylated Derivatives on a Solid Support: Synthesis of Hydroxamate-Based Pseudo-Peptides

Abstract

N-Hydroxyl-substituted amino acid derivatives are key building blocks for synthesis of hydroxamate-based pseudo-peptides. They have potentially important applications in the synthesis of peptidornimetics, enzyme inhibitors, natural products, and in combinatorial chemistry. Several methods for synthesis of N-hydroxylarnino acid derivatives in solution have been reported. But no method has been reported to our knowledge for the direct conversion of amino acids to their N-hydroxyl-substituted derivatives on a solid support. In our continuing efforts to constructing a library of metal-binding, hydroxamate-based pseudopeptide, we have been interested in developing a protocol for efficient conversion of amino acids to their corresponding N-hydroxylated derivatives on a solid support.