Detailed structure of lipid A isolated from lipopolysaccharide from the marine proteobacterium Marinomonas vaga ATCC 27119.
The chemical structure of a novel lipid A, the major component of the lipopolysaccharide from the marine gamma-proteobacterium Marinomonas vaga ATCC 27119(T), was determined by compositional analysis, NMR spectroscopy, and MS. It was found to be beta-1,6-glucosaminobiose 1-phosphate acylated with (R)-3-[dodecanoyl(dodecenoyl)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, 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-hydroxyalkanoic acid, distinguish M. vaga lipid A from other such molecules.
Krasikova
Inna N
IN
Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russia. innakras@piboc.dvo.ru
Kapustina
Natalie V
NV
Isakov
Vladimir V
VV
Dmitrenok
Andrey S
AS
Dmitrenok
Pavel S
PS
Gorshkova
Natalie M
NM
Solov'eva
Tamara F
TF
D000818:Animals; D001426:Bacterial Proteins / Q000737:chemistry* / Q000633:toxicity; D020563:Gammaproteobacteria / Q000737:chemistry*; D008050:Lipid A / Q000737:chemistry* / Q000633:toxicity; D008070:Lipopolysaccharides / Q000737:chemistry*; D013058:Mass Spectrometry; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012623:Seawater
D001426:Bacterial Proteins; D008050:Lipid A; D008070:Lipopolysaccharides