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

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)8304-8308
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number34
DOIs
Publication statusPublished - 2017 Jun 16

Fingerprint

Phosphorylation
Phospholipids
Inositol
Phosphatidylinositols
Chlorides
CD1d Antigen
Bearings (structural)
Glycolipids
Lipids
Derivatives
Molecules
naphthol BINOL

Keywords

  • Entamoeba histolytica
  • glycosylation
  • phospholipids
  • phosphorylation
  • synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Employing BINOL-Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica. / Aiba, Toshihiko; Suehara, Sae; Choy, Siew Ling; Maekawa, Yuuki; Lotter, Hannelore; Murai, Toshiaki; Inuki, Shinsuke; Fukase, Koichi; Fujimoto, Yukari.

In: Chemistry - A European Journal, Vol. 23, No. 34, 16.06.2017, p. 8304-8308.

Research output: Contribution to journalArticle

Aiba, Toshihiko ; Suehara, Sae ; Choy, Siew Ling ; Maekawa, Yuuki ; Lotter, Hannelore ; Murai, Toshiaki ; Inuki, Shinsuke ; Fukase, Koichi ; Fujimoto, Yukari. / Employing BINOL-Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica. In: Chemistry - A European Journal. 2017 ; Vol. 23, No. 34. pp. 8304-8308.
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AU - Choy, Siew Ling

AU - Maekawa, Yuuki

AU - Lotter, Hannelore

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AU - Inuki, Shinsuke

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