| Literature DB >> 16458002 |
Chengfeng Xia1, Qingjia Yao, Jens Schümann, Emmanuel Rossy, Wenlan Chen, Lizhi Zhu, Wenpeng Zhang, Gennaro De Libero, Peng George Wang.
Abstract
Glycoceramides can activate NKT cells by binding with CD1d to produce IFN-gamma, IL-4, and other cytokines. An efficient synthetic pathway for alpha-galactosylceramide (KRN7000) was established by coupling a protected galactose donor to a properly protected ceramide. During the investigation, it was discovered that when the ceramide was protected with benzyl groups, only beta-galactosylceramide was produced from the glycosylation reaction. In contrast, the ceramide with benzoyl protecting groups produced alpha-galactosylceramide. Isoglobotrihexosylceramide (iGb3) was prepared by glycosylation of Galalpha1-3Galbeta1-4Glc donor with 2-azido-sphingosine in high yield. Biological assays on the synthetic KRN7000 and iGb3 were performed using human and murine iNKT cell clones or hybridomas.Entities:
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Year: 2006 PMID： 16458002 DOI： 10.1016/j.bmcl.2006.01.040
Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823