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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.

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    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 02;13(17):4530-3

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    PMID: 21815670

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