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.
Chemistry. 2017 Jun 16;23(34):8304-8308. doi: 10.1002/chem.201701298. Epub 2017 May 24.
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.
报道了从溶组织内阿米巴中糖苷肌醇磷脂的化学合成。该合成的关键特征是通过磷硒酰氯对肌醇衍生物的不对称性进行区域选择性磷酸化反应。开发了一种新的保护基策略，利用烯丙基和Alloc 基团合成带有不饱和脂质的复杂糖脂。这些进展为各种复杂的肌醇磷脂及其类似物提供了有效的合成途径。此外，还评估了合成肌醇磷脂与小鼠 CD1d 分子的结合亲和力和免疫刺激活性。
