Peer-Reviewed Journal Details
Mandatory Fields
Pilgrim, W,Murphy, PV
2009
February
Organic Letters
alpha-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives
Published
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Optional Fields
STEREOSELECTIVE-SYNTHESIS NKT CELLS THIOGLYCOSIDE GLYCOLIPIDS ANTIGENS GLYCALS KRN7000 ANALOGS
11
939
942
Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.
DOI 10.1021/ol802915h
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