Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

D-3-Hydroxyte (3R)-3-hydroxytetradecanoic acid

Synonyms: CHEMBL1232858, CHEBI:42539, HMDB10731, AC1NRB5K, LMFA01050322, ...

Plötz, B.M. et al., Larsson, L. et al., Zähringer, U. et al.

Larsson, Szponar, Pehrson,

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High impact information on Tetradecanoic acid, 3-hydroxy-, (R)-

The lipid A consists of a beta-(1-->6)-linked 2,3-diamino-2,3-dideoxy-D-glucopyranose (DAG) disaccharide carrying two residues each of (R)-3-hydroxytetradecanoic acid and (R)-3-hydroxyhexadecanoic acid in amide linkage and one residue of octadecanoic acid in ester linkage [1].
We used a mass spectrometry-based assay for identifying the endotoxin (lipopolysaccharide, LPS) marker (R)-3-hydroxytetradecanoic acid in cigarette smoke particles and found that smoking involved inhalation of 17.4 pmol of endotoxin per each smoked cigarette [2].
It was found to be structurally distinct from the tetra-acyl lipid A biosynthetic precursor Ia (compound 406) in lacking the primary (R)-3-hydroxytetradecanoic acid 14:0(3-OH) in position 3' ester-linked to the 'non-reducing' glucosamine (GlcN II) [3].

References

Characterization of a novel lipid A containing D-galacturonic acid that replaces phosphate residues. The structure of the lipid a of the lipopolysaccharide from the hyperthermophilic bacterium Aquifex pyrophilus. Plötz, B.M., Lindner, B., Stetter, K.O., Holst, O. J. Biol. Chem. (2000) [Pubmed]
Tobacco smoking increases dramatically air concentrations of endotoxin. Larsson, L., Szponar, B., Pehrson, C. Indoor air. (2004) [Pubmed]
Structural and biological characterisation of a novel tetra-acyl lipid A from Escherichia coli F515 lipopolysaccharide acting as endotoxin antagonist in human monocytes. Zähringer, U., Salvetzki, R., Wagner, F., Lindner, B., Ulmer, A.J. J. Endotoxin Res. (2001) [Pubmed]

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