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The total synthesis of absolute anomeric confirmation α-galactosylceramide analogues from raffinose is described. Using the naturally occurring α-galactoside raffinose as the starting material, the easily maneuverable protocol without glycosylation reactions ensured the critical α-linkage in the product and simplified the synthetic procedures. The immunostimulatory activities of the new α-galactosylceramides were validated by both in vitro and in vivo NKT cell stimulation assays.


Zhenxing Zhang, Wei Zhao, Bin Wang, Chengfeng Xia, Wenpeng Zhang, Peng George Wang. The total synthesis of immunostimulant α-galactosylceramides from naturally configured α-galactoside raffinose. Organic letters. 2011 Sep 2;13(17):4530-3

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PMID: 21815670

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