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Dr. Sherif Ibrahim Metwally Ramadan :: Publications: |
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| Title: | 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: | |
| Full paper | Not Available |
| 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. |
