Immunomodulatory α-galactoglycosphingolipids:: Synthesis of a 2′-O-methyl-α-Gal-GSL and evaluation of its immunostimulating capacity
Immunomodulatory α-galactoglycosphingolipids:: Synthesis of a 2′-O-methyl-α-Gal-GSL and evaluation of its immunostimulating capacity
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DOI：
10.1002/ejoc.200300512
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发表时间：
2004-01-30
影响因子：
2.8
通讯作者：
Taramelli, D
中科院分区：
文献类型：
--
作者：
Barbieri, L;Costantino, V;Taramelli, D
本文报道了免疫刺激性α-半乳糖鞘脂1的2 ′-甲氧基类似物1-2-二十二烷酰氨基-O-（2-O-甲基-α-D-吡喃半乳糖基）-1，3，4-十八烷三醇（2）的全合成。利用改进的Mukaiyama反应首次成功地进行了鞘氨醇叠氮基前体的立体选择性α-糖基化。当在72小时脾细胞增殖试验中测定时，化合物2的刺激性显著低于未甲基化的化合物1，表明半乳糖2-OH基团对于α-Gal-GSL的免疫刺激活性是必需的。((C)Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2004）。
The total synthesis of 1-2-docosanoylamino-O-(2-O-methyl-alpha-D-galactopyranosyl)-1,3,4-octadecanetriol (2), a 2'-methoxy analog of the immunostimulating alpha-galactoglycosphingolipid 1, is reported. Stereoselective alpha-glycosylation of the azido precursor of sphingosine was successfully performed for the first time using an improved Mukaiyama reaction. When assayed in a 72 h splenocyte proliferation test, compound 2 was significantly less stimulatory than the non-methylated compound 1, suggesting that the galactose 2-OH group is essential for the immunostimulatory activity of alpha-Gal-GSLs. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).