Traceless solid-phase synthesis of chiral 3-aryl beta-amino acid containing peptides using a side-chain-tethered beta-amino acid building block.
[reaction: see text] A general method for the attachment of a chiral aromatic side-chain-containing beta-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 beta-amino acids with nonpolar side chains.
Lee
Y
Y
Department of Chemistry, Northwestern University, Evanston, Illinois 60208-3113, USA.
Silverman
R B
RB
D000596:Amino Acids / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*
D000596:Amino Acids; D010455:Peptides