| publication name | Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain |
|---|---|
| Authors | Weizhun Yang, Sherif Ramadan, Bo Yang, Keisuke Yoshida, and Xuefei Huang |
| year | 2016 |
| keywords | Glycopeptide, Sulfation, Stereoselectivity. |
| journal | The Journal of Organic Chemistry |
| volume | 81 |
| issue | 23 |
| pages | 12052 − 12059 |
| publisher | ACS Publications |
| Local/International | International |
| Paper Link | http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02441 |
| Full paper | download |
| Supplementary materials | Not Available |
Abstract
Among many hurdles in synthesizing proteo- glycan glycopeptides, one challenge is the incorporation of aspartic acid in the peptide backbone and acid sensitive O - sulfated glycan chains. To overcome this, a new strategy was developed utilizing homoserine as an aspartic acid precursor. The conversion of homoserine to aspartic acid in the glycopeptide was successfully accomplished by late stage oxidation using (2,2,6,6-tetramethyl-piperidin-1-yl)oxyl (TEMPO) and bis(acetoxy)iodobenzene (BAIB). This is the fi rst time that a glycopeptide containing aspartic acid and an O-sulfated glycan was synthesized.