Synthesis of Chiral Amino Acids with Metal Ion Chelating Side Chains from L-Serine using Negishi Cross-Coupling Reaction

Abstract

The scope of the Negishi cross-coupling reaction of organozinc compounds derived from chiral amino acids was extended to electron rich iodoanilines and iodobenzylamines as coupling reagents. The protocol allows the direct modification of serine into phenylalanine derivatives bearing metal ion chelating ligands in their side chain, such as amino esters 6 and 7. The preparation of metal complex labeled peptides, the construction of synthetic receptors and hybrid materials are potential applications of the modified chiral amino acids.