Issue 17, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
31 Jan 2014
Accepted
08 Mar 2014
First published
11 Mar 2014

Org. Biomol. Chem., 2014,12, 2729-2736

Author version available

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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