Synthesis and bioactivity of α-galactosylceramide analogues bearing an aryl group within the fatty amide chain

We describe the synthesis and bioactivity of analogues of α-galactosylceramide (1) bearing a long-chain alkyl group substituted at the meta or para position of an aryl group embedded within the amide chain. We compared the ability of these compounds and of 1 and C6Ph (2, which has a phenyl group at the amide chain terminus) to stimulate murine invariant Natural Killer T cells and to dock with human CD1d.