Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides
作者： Peter J. Jervis , Natacha Veerapen , Gabriel Bricard , Liam R. Cox , Steven A. Porcelli
DOI: 10.1016/J.BMCL.2010.05.010
关键词:
摘要: α-Glucosyl ceramides 4 and 5 have been synthesised evaluated for their ability to stimulate the activation expansion of human iNKT cells. The key challenge in synthesis both target molecules was stereoselective α-glycosidic linkage. Of methods examined, glycosylation using per-TMS-protected glucosyl iodide 16 completely α-selective provided gram quantities amine 11, from which α-glucosyl were obtained by N-acylation. α-GlcCer 4, containing a C24 saturated acyl chain, stimulated marked proliferation circulating cells short-term cultures. 5, contains C20 11,14-cis-diene chain (C20:2), induced extremely similar levels cell expansion.
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