247158-69-6Relevant articles and documents
Synthesis of13C-labeled biosynthetic precursor of lipid A and its analogue with shorter acyl chains
Oikawa, Masato,Shintaku, Tetsuya,Sekljic, Harald,Fukase, Koichi,Kusumoto, Shoichi
, p. 1857 - 1867 (2007/10/03)
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.