Tetrahedron Letters p. 6843 - 6847 (2000)
Update date:2022-08-03
Topics:
Sakai, Yasuhiro
Oikawa, Masato
Yoshizaki, Hiroaki
Ogawa, Tomohiko
Suda, Yasuo
Fukase, Koichi
Kusumoto, Shoichi
Synthesis of lipid A 1 isolated from Helicobacter pylori strain-206-1 has been achieved in 2.2% total yield through 14 steps from D-glucosamine by employing a p-(trifluoromethyl)benzyl group for protection of the hydroxy group on the 3-hydroxy fatty acid residue. The synthetic specimen was identical with the natural counterpart in chromatographic, spectroscopic, and biological aspects. A structural analogue 2 which lacks the ethanolamine residue of 1 was also synthesized, and 2 was found to exhibit less potent IL-1β-inducing activity than 1. (C) 2000 Elsevier Science Ltd.
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