New prototypical O-linked-glycopeptidomimetics corresponding to the linkage region of proteoglycans

A new class of glycopeptidomimetic composed of N-substituted oligoglycine (peptoid) mimicking the β-d-Xyl-(1 → 3)-O-l-Ser linkage region of proteoglycans was synthesized using a convergent approach. Reiterative N-alkylation-N-bromoacetylation reactions were used starting from tert-butyl bromoacetate (1) and isopropylamine. Perbenzoylated 2-aminoethyl β-d-xylopyranoside 10 constituted the key glycan l-Ser mimic.