Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides
Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides
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DOI：
10.1016/j.bmcl.2010.05.010
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发表时间：
2010-06-15
影响因子：
2.7
通讯作者：
Besra, Gurdyal S.
中科院分区：
文献类型：
--
作者：
Jervis, Peter J.;Veerapen, Natacha;Besra, Gurdyal S.
已经合成了α-葡萄糖基神经酰胺4和5，并评价了它们刺激人iNKT细胞活化和扩增的能力。合成两种靶分子的关键挑战是α-糖苷键的立体选择性合成。在检查的方法中，使用全TMS保护的葡糖基碘16的糖基化是完全α-选择性的，并提供克量的胺11，由此通过N-酰化获得α-葡糖基神经酰胺4和5。含有C24饱和酰基链的α-GlcCer 4在短期培养物中刺激人循环iNKT细胞的显著增殖和扩增。含有C20 11，14-顺式-二烯酰基链（C20：2）的α-GlcCer 5诱导极其相似水平的iNKT细胞活化和扩增。(C)2010爱思唯尔有限公司版权所有。
alpha-Glucosyl ceramides 4 and 5 have been synthesised and evaluated for their ability to stimulate the activation and expansion of human iNKT cells. The key challenge in the synthesis of both target molecules was the stereoselective synthesis of the alpha-glycosidic linkage. Of the methods examined, glycosylation using per-TMS-protected glucosyl iodide 16 was completely alpha-selective and provided gram quantities of amine 11, from which alpha-glucosyl ceramides 4 and 5 were obtained by N-acylation. alpha-GlcCer 4, containing a C24 saturated acyl chain, stimulated a marked proliferation and expansion of human circulating iNKT cells in short-term cultures. alpha-GlcCer 5, which contains a C20 11,14-cis-diene acyl chain (C20: 2), induced extremely similar levels of iNKT cell activation and expansion. (C) 2010 Elsevier Ltd. All rights reserved.