Automated Microwave-Enhanced Synthesis of Glycopeptides with O-Linked Glycans

Introduction

Glycosylation is an important post-translational and cotranslational modification that involves the covalent modification of proteins or peptides with mono, di, or oligosaccharides. Glycoproteins have diverse biological functions ranging from structural proteins and hormones (like collagen and thyroidstimulating hormone) to enzymes and proteins involved in regulating immune response (such as various phosphatases and antibodies). As the critical role of glycosylation becomes further illuminated, interest in the chemical synthesis of glycopeptides continues to grow steadily. Peptides containing O-glycosylated amino acids can be prepared by SPPS by using Fmoc protected Ser or Thr. Application of microwave energy to the synthesis of glycopeptides containing O-linked glycans allows for more efficient coupling which leads to rapid synthesis times and high purity (CarboMAX^TM).