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Chemical synthesis of sulfated-?(1?6)-D-mannopyranan |
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| รหัสดีโอไอ | |
| Creator | 1. Warunda Bunthitsakda 2. Chakree Wattanasiri 3. Somsak Ruchirawat 4. Siwarutt Boonyarattanakalin |
| Title | Chemical synthesis of sulfated-?(1?6)-D-mannopyranan |
| Publisher | Research and Development Office, Prince of Songkla University |
| Publication Year | 2562 |
| Journal Title | Songklanakarin Journal of Science and Technology |
| Journal Vol. | 41 |
| Journal No. | 4 |
| Page no. | 795-803 |
| Keyword | sulfated oligosaccharides, PI-88 analogue, sulfation, sulfur trioxide-pyridine complex, rapid synthesis |
| URL Website | http://rdo.psu.ac.th/sjstweb/index.php |
| ISSN | 0125-3395 |
| Abstract | Sulfated oligosaccharides are a group of compounds with important biological properties as drug molecules. Phosphomannopentaose sulfate (PI-88) is a sulfated oligosaccharide with antitumor properties. PI-88 has been thoroughly investigated as a drug candidate to treat cancers, and it showed promising results in Phase 1 and Phase 2 clinical trials. The glycosidic linkages for the sulfated mannan in PI-88 are mainly of ?(1?3) and ?(1?2) types. It is important to determine whether the specific glycosidic linkages connecting the sulfated mannan are crucial for the biological activities of PI-88. Therefore, this study explores a method to rapidly synthesize sulfated mannan with ?(1?6)linkages. We report here the rapid synthesis of sulfated-?-D-mannopyranan, a PI-88 analogue, by using a regio- and stereocontrolled polymerization of a mannosyl tricyclic orthoester. After the global protecting group removal, the sulfation was successfully carried out by treatment of the unmasked mannans with sulfur trioxide-pyridine complex in dimethyl formamide. |
