title: Syntheses of 1-O-[5-(carboxy)pentanoyl]-2-deoxy-2-(2,2- difluorotetradecanamido)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-4- O- phosphono-alpha-D-glucopyranose and its analogues.
abstract: 1-O-[5-(Carboxy)pentanoyl]-2-deoxy-2-(2,2-difluorotetradecanamido) -3-O- [(R)-3-(tetradecanoyl-oxy)tetradecanoyl]-4-O-phosphono-alpha-D-glucop yranos e (13) and its analogues (16 and 19) were synthesized. Compound 13 showed strong LPS-agonistic activity.
authors.affiliation: Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Shiozaki
authors.forename: H
authors.initials: H
authors.lastname: Miyazaki
authors.forename: M
authors.initials: M
authors.lastname: Arai
authors.forename: T
authors.initials: T
authors.lastname: Hiraoka
authors.forename: S
authors.initials: S
authors.lastname: Kurakata
authors.forename: T
authors.initials: T
authors.lastname: Tatsuta
authors.forename: J
authors.initials: J
authors.lastname: Ogawa
authors.forename: M
authors.initials: M
authors.lastname: Nishijima
authors.forename: Y
authors.initials: Y
authors.lastname: Akamatsu
mesh_terms: D000818:Animals; D002240:Carbohydrate Sequence; D002460:Cell Line; D004926:Escherichia coli; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors*; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D008969:Molecular Sequence Data; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis
chemical_list: C093464:1-O-(5-(carboxy)pentanoyl)-2-deoxy-2-(2,2-difluorotetradecanamido)-3-O-(3-(tetradecanoyloxy)tetradecanoyl)-4-O-phosphonoglucopyranose; D008050:Lipid A; D008070:Lipopolysaccharides; D014409:Tumor Necrosis Factor-alpha