The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids

Complex mixtures of natural dimycoloyl diarabinoglycerols isolated from mycobacteria have been shown to be both potent immune signalling agents and potentially valuable antigens in the serodiagnosis of mycobacterial infections. We now report the highly stereocontrolled synthesis of diacyl L-glycerol-(1' -> 1)-beta-D-arabinofuranosyl-alpha-D-arabinofuranosides based on simple fatty acids and single defined synthetic mycolic acids. NMR analysis confirmed that the synthetic core was identical to that in natural mixtures.