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

Toshihiko Aiba, Sae Suehara, Siew Ling Choy, Yuuki Maekawa, Hannelore Lotter, Toshiaki Murai, Shinsuke Inuki, Koichi Fukase, Yukari Fujimoto

研究成果: Article

8 引用 (Scopus)

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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.

元の言語English
ページ(範囲)8304-8308
ページ数5
ジャーナルChemistry - A European Journal
23
発行部数34
DOI
出版物ステータスPublished - 2017 6 16

ASJC Scopus subject areas

  • Chemistry(all)

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