کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1374951 | 981928 | 2006 | 5 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Synthesis and biological evaluation of α-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3) Synthesis and biological evaluation of α-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3)](/preview/png/1374951.png)
Glycoceramides can activate NKT cells by binding with CD1d to produce IFN-γ, IL-4, and other cytokines. An efficient synthetic pathway for α-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 β-galactosylceramide was produced from the glycosylation reaction. In contrast, the ceramide with benzoyl protecting groups produced α-galactosylceramide. Isoglobotrihexosylceramide (iGb3) was prepared by glycosylation of Galα1-3Galβ1-4Glc 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.
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Journal: Bioorganic & Medicinal Chemistry Letters - Volume 16, Issue 8, 15 April 2006, Pages 2195–2199