Bulletin of the Chemical Society of Japan p. 1857 - 1867 (1999)
Update date:2022-09-26
Topics:
Oikawa, Masato
Shintaku, Tetsuya
Sekljic, Harald
Fukase, Koichi
Kusumoto, Shoichi
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.
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