Synthesis of13C-labeled biosynthetic precursor of lipid A and its analogue with shorter acyl chains

Article abstract of DOI:10.1246/bcsj.72.1857

The synthesis of regiospecifically ¹³C-labeled compounds of a biosynthetic precursor of lipid A and its analogue with shorter acyl chains is described. D-(6-¹³C)Glucose was converted into a suitably protected glucosamine derivative via 1,6-anhydro-β-D-(6-¹³C)glucose. After coupling with glycosyl donors, the desired compounds were synthesized through a 6-step reaction sequence. The total yields were 1.7% for the biosynthetic precursor, and 6.4% for the short acyl analogue, respectively, for a total of 18 steps from D-(6-¹³C)glucose.