29 高度好熱菌Thermus thermophilus糖脂質の全合成と免疫刺激活性(口頭発表の部)

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An extreme thermophile, Thermus thermophilus HB8 is a microorganism living in a severe hot environment. Recently, three kinds of glycolipid have been extracted from the cell membrane of the microorganism, and these structures have been determined. All these glycolipids showed immunostimulating activities. In order to examine the detailed biological activities and to search the immunostimulatory mechanism, we synthesized the most unique glycolipids, phosphoglycolipid 1a, by applying newly developed α-selective glycosylation. The synthetic scheme is shown in Scheme 1. First, we examined the α-selective glycosylation of 2-azide sugar 2 and the glyceric acid unit 3. We used the 2-azide sugar, 3,4,6-tri-O-benzyloxy-2-azide-D-glucopyranosides, without the neighboring group effect at 2-position, as the form of 3-nitro-2-pyridyl glycoside. The 3-nitro-2-pyridyl glycoside is easily activated with a catalytic amount of Lewis acid, and we were able to obtain the α-glycoside 4 as the major compound. The α-glycoside was then provided to the phosphorylation with phosphoroamidite 6a to construct the skeleton. Final deprotection with reductive conditions successfully afforded the desired compound 1a. We also synthesized the diastereomer 1b, which has the different configuration at the diacyl glycerol moiety. Only 1a showed the immunostimulatory activity, suggesting the existence of a receptor that recognizes diacyl glycerol part.
天然有機化合物討論会の論文
2007-08-24

29 高度好熱菌Thermus thermophilus糖脂質の全合成と免疫刺激活性(口頭発表の部)

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