Synthesis of 2-deoxy-2-[(2R,3S)-2-fluoro-3-hydroxytetradecanamido]- 3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-D-glucopyranose and its (2S,3R)-isomer.
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.
Shiozaki
M
M
New Lead Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Arai
M
M
Hiraoka
T
T
Nishijima
M
M
Akamatsu
Y
Y
D002240:Carbohydrate Sequence; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000378:metabolism; D008262:Macrophage Activation; D008264:Macrophages / Q000378:metabolism; D008969:Molecular Sequence Data; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives; D013237:Stereoisomerism
D008050:Lipid A; D008070:Lipopolysaccharides; C083942:2-deoxy-2-(2-fluoro-3-hydroxytetradecanamido)-3-O-(3-hydroxytetradecanoyl)-4-O-phosphonoglucopyranose; D011761:Pyrrolidonecarboxylic Acid