Employing BINOL-Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica
| Autor: | Toshiaki Murai, Hannelore Lotter, Toshihiko Aiba, Siew Ling Choy, Shinsuke Inuki, Sae Suehara, Yuuki Maekawa, Koichi Fukase, Yukari Fujimoto |
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| Rok vydání: | 2017 |
| Předmět: |
Stereochemistry
Glycosylphosphatidylinositols Phospholipid Naphthols 010402 general chemistry Phosphatidylinositols 01 natural sciences Desymmetrization Chemical synthesis Catalysis Entamoeba histolytica chemistry.chemical_compound Glycolipid Inositol Glycosyl Phosphorylation biology 010405 organic chemistry Chemistry Organic Chemistry General Chemistry biology.organism_classification 0104 chemical sciences carbohydrates (lipids) Biochemistry Inositol phosphorylation lipids (amino acids peptides and proteins) |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 23(34) |
| ISSN: | 1521-3765 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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