Chemical Synthesis of Glycopeptides containing L-Arabinosylated Hydroxyproline and Sulfated Tyrosine

Post-translationally modified peptides are important regulating molecules for living organisms. Here we report the stereoselective total synthesis of beta-1,2-linked L-arabinosylated Fmoc-protected hydroxyproline building blocks and their incorporation, together with sulfated tyrosine and hydroxyproline, into the plant peptide hormone PSY1. Clean glycopeptides were obtained by perform-ing acetyl removal from the L-arabinose groups prior to deprotection of the neopentyl-protected sulfated tyrosine.