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The total synthesis of immunostimulant ?-galactosylceramides from naturally configured ?-galactoside raffinose.

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

SUBMITTER: Zhang Z

PROVIDER: S-EPMC3398385 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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The total synthesis of immunostimulant α-galactosylceramides from naturally configured α-galactoside raffinose.

Zhang Zhenxing Z Zhao Wei W Wang Bin B Xia Chengfeng C Zhang Wenpeng W Wang Peng George PG

Organic letters 20110804 17

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. ...[more]

PMID: 21815670

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