Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Employing BINOL-Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica

Employing BINOL-Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica
Koichi Fukase, Hannelore Lotter, Yuuki Maekawa, Toshihiko Aiba, Sae Suehara, Siew-Ling Choy, Toshiaki Murai, Shinsuke Inuki, Yukari Fujimoto
The chemical synthesis of glycosyl inositol phospholipids from Entamoeba histolytica is reported. The key feature of this synthesis is a regioselective phosphorylation reaction that occurs through desymmetrization of a myo-inositol derivative with phosphoroselenoyl chloride. A new protecting-group strategy was developed that utilizes allyl and alloc groups to synthesize complex glycolipids bearing unsaturated lipids. These developments provided an efficient synthetic route for various complex inositol phospholipids and their analogues. Furthermore, the binding affinity of the synthetic inositol phospholipids with mouse CD1d molecules has been evaluated, as well as the immunostimulatory activity. A route to glycolipids: The synthesis of glycosyl inositol phospholipids from Entamoeba histolytica is reported, the key feature of which is a regioselective phosphorylation reaction that occurs through desymmetrization of a myo-inositol derivative with phosphoroselenoyl chloride. A new protecting-group strategy was developed to synthesize complex glycolipids bearing unsaturated lipids. This provided an efficient route to various complex inositol phospholipids and their analogues.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701298

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