Buba, Annette E.Annette E.BubaLöwe, HolgerHolgerLöweKunz, HorstHorstKunz2022-03-052022-03-052015https://publica.fraunhofer.de/handle/publica/24100510.1002/ejoc.201500929Peptide antibiotics often contain N-methylated amino acids. These N-methylamino components enhance the metabolic stability and strongly influence the conformational behavior of these peptide drugs. N-Methyl-O-glycosyl amino acids, in particular, threonine and serine derivatives, are unknown so far. Fmoc-protected N-methyl-O-glycosyl-threonine and -serine building blocks, including sialyl TN antigens, have been synthesized for the first time by converting the Fmoc-protected O-glycosyl amino acids or their tert-butyl esters into the corresponding oxazolidinones followed by reductive ring-opening. These new components are considered interesting for the construction of modified mucin glycopeptide anti-tumor vaccines with extended biological half-life.ensolid-phase synthesisglycopeptidesAmino acidsAntigens547journal article