title: Employing BINOL-Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica.
abstract: 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.
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.|Department of Chemistry, Graduate school of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Aiba
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Sae
authors.initials: S
authors.lastname: Suehara
authors.affiliation: Bernhard Nocht Institute for Tropical Medicine, Bernhard-Nocht-Str.74, Hamburg, 20359, Germany.
authors.forename: Siew-Ling
authors.initials: SL
authors.lastname: Choy
authors.affiliation: Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu, 501-1193, Japan.
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Maekawa
authors.affiliation: Bernhard Nocht Institute for Tropical Medicine, Bernhard-Nocht-Str.74, Hamburg, 20359, Germany.
authors.forename: Hannelore
authors.initials: H
authors.lastname: Lotter
authors.affiliation: Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu, 501-1193, Japan.
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Murai
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Shinsuke
authors.initials: S
authors.lastname: Inuki
authors.affiliation: Department of Chemistry, Graduate school of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Fukase
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Yukari
authors.identifier: http://orcid.org/0000-0001-5320-3192
authors.initials: Y
authors.lastname: Fujimoto
mesh_terms: D004748:Entamoeba histolytica / Q000737:chemistry*; D017261:Glycosylphosphatidylinositols / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D010716:Phosphatidylinositols / Q000138:chemical synthesis*; D010766:Phosphorylation
chemical_list: C406944:BINOL, naphthol; D017261:Glycosylphosphatidylinositols; D009284:Naphthols; D010716:Phosphatidylinositols
keywords: Entamoeba histolytica; glycosylation; phospholipids; phosphorylation; synthetic methods