Detailed structure of lipid A isolated from lipopolysaccharide from the marine proteobacterium Marinomonas vaga ATCC 27119T

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Abstract

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 β-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.

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