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Issue 17, 2014
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A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate

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Abstract

Isoglobotrihexosylceramide (iGb3, 1) is an immunomodulatory glycolipid that binds to CD1d and is presented to the T-cell receptor (TCR) of invariant natural killer T (iNKT) cells. To investigate how modifications to the lipid tail or terminal sugar residue of iGb3 influence iNKT cell activity, we developed an efficient and divergent synthetic route that provided access to both sugar and lipid iGb3 analogues which utilised a lactosyl 2-azido-sphingosine derivative as a common intermediate. In this way, iGb3 (1) and the unprecedented analogues 6′′′-deoxy-iGb3-sphingosine 2, 6′′′-deoxy-iGb3-sphinganine 3, C12 N-acyl iGb3 4 and C20:2 N-acyl iGb3 5 were prepared so that key structure–activity relationships can be explored.

Graphical abstract: A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate

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Publication details

The article was received on 31 Jan 2014, accepted on 08 Mar 2014 and first published on 11 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00241E
Citation: Org. Biomol. Chem., 2014,12, 2729-2736
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    A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate

    J. M. H. Cheng, E. M. Dangerfield, M. S. M. Timmer and B. L. Stocker, Org. Biomol. Chem., 2014, 12, 2729
    DOI: 10.1039/C4OB00241E

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