Shiozaki M, Arai M, Hiraoka T, Nishijima M, Akamatsu Y
New Lead Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Biosci Biotechnol Biochem. 1993 Sep;57(9):1526-9. doi: 10.1271/bbb.57.1526.
2-Deoxy-2-[(2R,3S)-2-fluoro-3-hydroxytetradecanamido]-3-O-[( 3R)-3-hydroxytetradecanoyl]-4-O-phosphono-D-glucopyranose and its (2S,3R)-isomer were respectively synthesized from allyl 2-[(2R,3S)-3-(benzyloxycarbonyloxy)-2-fluorotetradecanamido] -2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside and its corresponding (2S,3R)-isomer. Both target compounds did not activate macrophage, but the (2S,3R)-analogue strongly inhibited the binding of LPS to macrophage.