Traceless solid-phase synthesis of chiral 3-aryl β-amino acid containing peptides using a side-chain-tethered β-amino acid building block

(matrix presented) A general method for the attachment of a chiral aromatic side-chain-containing β-amino acid to a polymer support using a traceless silyl linkage strategy has been developed. Using this building block, solid-phase synthesis was carried out to obtain tripeptide analogues with the aromatic ring either unsubstituted or halogenated (Br, I) at the position of the silyl group. The building blocks could generate libraries of peptidomimetics or cyclic peptides containing β-amino acids with nonpolar side chains.