Efficient Synthesis of a Phosphinate Bis-Amino Acid and Its Use in the Construction of Amphiphilic Peptides

Article abstract of DOI:10.1021/jo00094a036

A new amphiphilic bis-amino acid has been designed and its convergent, asymmetric synthesis achieved in differentially protected form.A convenient preparation of iodophenylalanine, a generally useful starting material, is disclosed.Sequential palladium-catalyzed couplings of aryl iodides to phosphinate lead directly to the target protected bis-amino acid.Controlled peptide coupling of the new bis-amino acid is also demonstrated.