tailieunhanh - Báo cáo khoa học: Detailed structure of lipid A isolated from lipopolysaccharide from the marine proteobacterium Marinomonas vaga ATCC 27119T

The chemical structure of a novel lipid A, the major com-ponent of the lipopolysaccharide from the marine gamma-proteobacteriumMarinomonas vagaATCC 27119 T ,was determined by compositional analysis, NMR spectroscopy, and MS. It was found to be b-1,6-glucosaminobiose 1-phosphate acylated with (R)-3-[dodecanoyl(dodece-noyl)oxy]decanoic acid {C10 : 0 (3O-C12 : 0 [3O-C12 : 1])} or (R)-3-(decanoyloxy)decanoic acid [C10 : 0 (3O-C10 : 0)], (R)-3-hydroxydecanoic acid [C10 : 0 (3OH)], and (R)-3-[(R)-3-hydroxydecanoyloxy]decanoic acid (C10 : 0 {3O-[C10 : 0 (3OH)]}) at the 2, 3, and2¢positions, respectively | Eur. J. Biochem. 271 2895-2904 2004 FEBS 2004 doi Detailed structure of lipid A isolated from lipopolysaccharide from the marine proteobacterium Marinomonas vaga ATCC 27119T Inna N. Krasikova1 Natalie V. Kapustina1 Vladimir V. Isakov1 Andrey S. Dmitrenok2 Pavel S. Dmitrenok1 Natalie M. Gorshkova1 and Tamara F. Solov eva1 1Pacific Institute of Bioorganic Chemistry Far East Branch of the Russian Academy of Sciences Vladivostok Russia 2Suntory Institute for Bioorganic Research Osaka Japan The chemical structure of a novel lipid A the major component of the lipopolysaccharide from the marine gamma-proteobacterium Marinomonas vaga ATCC 27119T was determined by compositional analysis NMR spectroscopy and MS. It was found to be b-1 6-glucosaminobiose 1-phosphate acylated with R -3- dodecanoyl dodece-noyl oxy decanoic acid C10 0 3O-C12 0 3O-C12 1 or R -3- decanoyloxy decanoicacid C10 0 3O-C10 0 R -3-hydroxydecanoic acid C10 0 3OH and R -3- R -3-hydroxydecanoyloxy decanoic acid C10 0 3O- C10 0 3OH at the 2 3 and 2 positions respectively. It showed low lethal toxicity which is probably related to specific structural attributes. The absence of a fatty acid at the 3 position and a phosphoryl group at the 4 position and also the presence of an amide-linked R -3-hydroxyalkanoic acid that is further O-acylated with another R -3-hydroxy-alkanoic acid distinguish M. vaga lipid A from other such molecules. Keywords fast-atom bombardment MS FAB-MS lipid A marine proteobacteria Marinomonas vaga NMR. Gram-negative bacteria along with classical membrane lipids based on glycerol contain an unusual glycophospholipid known as lipid A. Functioning as a lipid anchor for lipopolysaccharide LPS it is one of the main components of the outer membrane of bacteria 1 making it important for maintenance of the normal physiology and growth of micro-organisms 2 . LPSs O-antigens and endotoxins of Gram-negative bacteria constitute a specific class of biopolymers that .