192444-73-8Relevant academic research and scientific papers
Synthetic chemistry and function of bacterial cell surface glycoconjugates
Kusumoto, Shoichi,Fukase, Koichi,Oikawa, Masato,Suda, Yasuo
, p. 453 - 458 (2002)
Typical bacterial glycoconjugates are known to stimulate immunological systems of higher animals and thereby play important roles in the primary defense of animals against bacterial infection. Lipopolysaccharide (LPS) of gram-negative bacteria is a representative of such glycoconjugates. LPS was first discovered as a potent bacterial toxin and named endotoxin but was soon found to exhibit immunostimulating activity. By the use of our synthetic pure preparations, the lipophilic partial structure of LPS, designated lipid A, proved to be the active entity responsible for both endotoxic and immunostimulating activities of LPS. This paper deals with our recent chemical synthesis and functional study of lipid A and related compounds. Synthesis is described of its various structural analogues, radio-labeled compound and Re-type LPS that contains two additional sugar moieties linked to lipid A.
Synthesis of an analog of biosynthetic precursor la of lipid A by an improved method: A novel antagonist containing four (S)-3-hydroxy fatty acids
Fukase, Koichi,Liu, Wen-Chi,Suda, Yasuo,Oikawa, Masato,Wada, Akira,Mori, Saeko,Ulmer, Arthur J.,Rietschel, Ernst Th.,Kusumoto, Shoichi
, p. 7455 - 7458 (1995)
Synthesis of an analog of a biosynthetic precursor of lipid A containing four (S)-3-hydroxytetradecanoic acids was effected via an improved synthetic route to investigate the relationship between the bioactivity and the chirality of the 3-hydroxy fatty acid residues in lipid A. The S-analog inhibited endotoxin-induced interleukin-6 (IL-6) production from human peripheral whole blood cells more strongly than the natural-type biosynthetic precursor with (R)-hydroxy acids, a known antagonist of LPS-induced cytokine release in human peripheral blood mononuclear cells.
Enzymatic preparation of (S)-3-hydroxytetradecanoic acid and synthesis of unnatural analogues of lipid A containing the (S)-acid
Liu, Wen-Chi,Oikawa, Masato,Fukase, Koichi,Suda, Yasuo,Winarno, Hendig,Mori, Saeko,Hashimoto, Masahito,Kusumoto, Shoichi
, p. 1441 - 1450 (2007/10/03)
Synthesis of unnatural analogues, that contain (S)-3-hydroxytetradecanoyl moieties in place of the corresponding natural (R)-isomers, of both lipid A and its biosynthetic precursor, designated precursor Ia or lipid IV(A), has been achieved through our recently developed procedure. (S)-3-Hydroxytetradecanoic acid was prepared from its racemate through the optical resolution by the use of a lipase and subsequent fractional recrystallization. The (S)-acyl analogue of lipid A exhibited slightly stronger interleukin-6 inducing activity than the corresponding natural lipid A, and the (S)-acyl analogue of the biosynthetic precursor was far more active than the natural precursor in inhibiting the induction of interleukin-6 by lipopolysaccharide.
