SYNTHESIS OF AN ANALOG OF BIOSYNTHETIC PRECURSOR IA OF LIPID-A BY AN IMPROVED METHOD - A NOVEL ANTAGONIST CONTAINING 4 (S)-3-HYDROXY FATTY-ACIDS

被引:26
作者
FUKASE, K [1 ]
LIU, WC [1 ]
SUDA, Y [1 ]
OIKAWA, M [1 ]
WADA, A [1 ]
MORI, S [1 ]
ULMER, AJ [1 ]
RIETSCHEL, ET [1 ]
KUSUMOTO, S [1 ]
机构
[1] FORSCHUNGSINST BORSTEL,D-23845 BORSTEL,GERMANY
关键词
D O I
10.1016/0040-4039(95)01433-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
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收藏
页码:7455 / 7458
页数:4
相关论文
共 16 条
[1]   E5531, A PURE ENDOTOXIN ANTAGONIST OF HIGH POTENCY [J].
CHRIST, WJ ;
ASANO, O ;
ROBIDOUX, ALC ;
PEREZ, M ;
WANG, YA ;
DUBUC, GR ;
GAVIN, WE ;
HAWKINS, LD ;
MCGUINNESS, PD ;
MULLARKEY, MA ;
LEWIS, MD ;
KISHI, Y ;
KAWATA, T ;
BRISTOL, JR ;
ROSE, JR ;
ROSSIGNOL, DP ;
KOBAYASHI, S ;
HISHINUMA, L ;
KIMURA, A ;
ASAKAWA, N ;
KATAYAMA, K ;
YAMATSU, I .
SCIENCE, 1995, 268 (5207) :80-83
[2]   MODULATION OF LIPOPOLYSACCHARIDE-INDUCED PRODUCTION OF TUMOR-NECROSIS-FACTOR, INTERLEUKIN-1, AND INTERLEUKIN-6 BY SYNTHETIC PRECURSOR-IA OF LIPID-A [J].
FEIST, W ;
ULMER, AJ ;
WANG, MH ;
MUSEHOLD, J ;
SCHLUTER, C ;
GERDES, J ;
HERZBECK, H ;
BRADE, H ;
KUSUMOTO, S ;
DIAMANTSTEIN, T ;
RIETSCHEL, ET ;
FLAD, HD .
FEMS MICROBIOLOGY IMMUNOLOGY, 1992, 89 (02) :73-89
[3]  
FUKASE K, 1994, J ENDOTOXIN RES, V1, P149
[4]  
HEINE H, 1994, J ENDOTOXIN RES, V1, P14
[5]   TOTAL SYNTHESIS OF ESCHERICHIA-COLI LIPID-A, THE ENDOTOXICALLY ACTIVE PRINCIPLE OF CELL-SURFACE LIPOPOLYSACCHARIDE [J].
IMOTO, M ;
YOSHIMURA, H ;
SHIMAMOTO, T ;
SAKAGUCHI, N ;
KUSUMOTO, S ;
SHIBA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) :2205-2214
[6]   CHEMICAL SYNTHESIS OF A BIOSYNTHETIC PRECURSOR OF LIPID-A WITH A PHOSPHORYLATED TETRAACYL DISACCHARIDE STRUCTURE [J].
IMOTO, M ;
YOSHIMURA, H ;
YAMAMOTO, M ;
SHIMAMOTO, T ;
KUSUMOTO, S ;
SHIBA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) :2197-2204
[7]   SYNTHETIC APPROACH TO LIPID-A - PREPARATION OF PHOSPHORYLATED DISACCHARIDES CONTAINING (R)-3-HYDROXYACYL AND (R)-3-ACYLOXYACYL GROUPS [J].
INAGE, M ;
CHAKI, H ;
IMOTO, M ;
SHIMAMOTO, T ;
KUSUMOTO, S ;
SHIBA, T .
TETRAHEDRON LETTERS, 1983, 24 (19) :2011-2014
[8]   CHEMICAL INACTIVATION OF LIPASE IN ORGANIC-SOLVENT - A LIPASE FROM PSEUDOMONAS-AERUGINOSA TE3285 IS MORE LIKE A TYPICAL SERINE ENZYME IN AN ORGANIC-SOLVENT THAN IN AQUEOUS-MEDIA [J].
NAKATANI, T ;
HIRATAKE, J ;
YOSHIKAWA, K ;
NISHIOKA, T ;
ODA, J .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1992, 56 (07) :1118-1123
[9]   IODINE AS A REAGENT FOR THE READY HYDROLYSIS OF PROP-1-ENYL GLYCOSIDES, OR THEIR CONVERSION INTO OXAZOLINES [J].
NASHED, MA ;
ANDERSON, L .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (21) :1274-1276
[10]  
OLTVOORT JJ, 1981, SYNTHESIS-STUTTGART, P305