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

European Journal of Biochemistry
Inna N KrasikovaTamara F Solov'eva

Abstract

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.

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Citations

Feb 27, 2010·Journal of the American Society for Mass Spectrometry·Jace W JonesRobert K Ernst
Apr 19, 2011·The Journal of Biological Chemistry·Nancy J PhillipsBradford W Gibson
Jul 8, 2009·Journal of Bacteriology·D Scott SnyderBrian Palenik
Jul 14, 2010·Biochemistry. Biokhimii︠a︡·D S Kabanov, I R Prokhorenko
Jun 21, 2013·Marine Drugs·Tamara Solov'evaIrina Yermak
May 9, 2008·Marine Drugs·Serena LeoneAntonio Molinaro
Jul 25, 2014·Marine Drugs·Reindert NijlandJos A G van Strijp
Oct 18, 2006·Bioorganicheskaia khimiia·E V Vorob'evaT F Solov'eva
Feb 13, 2019·Infection and Immunity·Toby L BartholomewJosé A Bengoechea

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