Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain

• DOI: 10.1021/acs.joc.6b02441
• Publication Date: 2016-11-03T20:53:27Z
• Authors: Weizhun Yang; Sherif Ramadan; Bo Yang; Keisuke Yoshida; Xuefei Huang
• Keywords: Aspartic acid; Homoserine

Among many hurdles in synthesizing proteoglycan glycopeptides, one challenge is the incorporation of aspartic acid peptide backbone and sensitive O-sulfated glycan chains. To overcome this, a new strategy was developed utilizing homoserine as an precursor. The conversion to glycopeptide successfully accomplished by late stage oxidation using (2,2,6,6-tetramethyl-piperidin-1-yl)oxyl (TEMPO) bis(acetoxy)iodobenzene (BAIB). This first time that containing synthesized.