Figure 1. Glycolipid structures and synthesis of C4” amide linked derivatives of α-GalCer.
A) KRN7000 is the prototypical α-GalCer antigen for iNKT cells. AH10-7 is a C6”-modified α-GalCer prepared and evaluated by us previously. Compounds 1–7 are representative C4”-modified α-GalCer derivatives previously described in the literature (see text for references). Amides 8–10 are the focus of this work. B) Synthetic strategy for the preparation of 8–10.