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Synlett 1996; 1996(3): 252-254
DOI: 10.1055/s-1996-5394
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Synthetic Study of a Bioactive 3H-Labeled Analogue of Lipid A

Koichi Fukase1 , Ikuko Kinoshita, Yasuo Suda, Yutaka Aoki, Wen-Chi Liu, Masato Oikawa, Motohiro Kurosawa, Ulrich Zähringer, Ulrich Seydel, Ernst Th. Rietschel, Shoichi Kusumoto2
  • 1Department of Chemistry, Faculty of Science, Osaka University, Toyonaka, Osaka 560, Japan, Fax 06 850 5419, Internet koichi@chem.sci.osaka-u.ac.jp
  • 2Department of Chemistry, Faculty of Science, Osaka University, Toyonaka, Osaka 560, Japan, Fax 06 850 5419
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Publication History

Publication Date:
31 December 2000 (online)

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A radio-labeled bioactive lipid A derivative was synthesized for the first time by 3H-labeling of a phosphonooxyethyl (PE) analogue. 3H-Labeling was effected via oxidation of the distal hydroxyl group of the ethylene glycol unit of a disaccharide intermediate and subsequent reduction of the resulting aldehyde by NaB3H4. Phosphorylation of the labeled alcohol and deprotection gave the target compound. The glycosidation of an ethylene glycol unit with a thioglycoside was promoted by PhIO-SnCl4-AgClO4 to give the α-glycoside selectively.

lipid A - tritium labeling - phosphonooxyethyl analogue - endotoxin - thioglycoside