86559-73-1
Chemical Structure
Lipid X
- CAS No.: 86559-73-1
- Formula:C34H66NO12P
- Molecular Weight:711.86
IUPAC Name: (2R,3S,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5-((R)-3-hydroxytetradecanamido)-6-(phosphonooxy)tetrahydro-2H-pyran-4-yl (R)-3-hydroxytetradecanoate
InChIKey: HEHQDWUWJVPREQ-XQJZMFRCSA-N
SMILES: O[C@H]1[C@H](OC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H](NC(C[C@H](O)CCCCCCCCCCC)=O)[C@@H](OP(O)(O)=O)O[C@@H]1CO
Biological Activity:
Lipid X is a 2,3-diacylglucosamine-1-phosphate that serves as the monosaccharide precursor of lipid A, possessing both LPS antagonist and weak agonist activities. Lipid X exerts protective effects by inhibiting tumor necrosis factor production, monocyte procoagulant activity, and neutrophil priming. Lipid X may induce transient pulmonary hypertension, neutropenia, and mild pyrogenic effects in laboratory animals. Lipid X has low toxicity and no in vitro antibacterial activity, but it significantly reduces mortality following Gram-negative bacterial infection and endotoxin exposure. Lipid X tends to accumulate in liver tissue, binds to circulating cellular components, and can be converted to lipid Y through transesterification. Lipid X can be used in research on Gram-negative bacterial sepsis, endotoxemia, and associated pulmonary hypertension[1][2][3][4].
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Lipid X | Lipid X is a 2,3-diacylglucosamine-1-phosphate that serves as the monosaccharide precursor of lipid A, possessing both LPS antagonist and weak agonist activities. Lipid X exerts protective effects by inhibiting tumor necrosis factor production, monocyte procoagulant activity, and neutrophil priming. Lipid X may induce transient pulmonary hypertension, neutropenia, and mild pyrogenic effects in laboratory animals. Lipid X has low toxicity and no in vitro antibacterial activity, but it significantly reduces mortality following Gram-negative bacterial infection and endotoxin exposure. Lipid X tends to accumulate in liver tissue, binds to circulating cellular components, and can be converted to lipid Y through transesterification. Lipid X can be used in research on Gram-negative bacterial sepsis, endotoxemia, and associated pulmonary hypertension. |
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References
- [1]. Brozek K A, et al. Biosynthesis of lipid A precursors in Escherichia coli. A membrane-bound enzyme that transfers a palmitoyl residue from a glycerophospholipid to lipid X[J]. Journal of Biological Chemistry, 1987, 262(11): 5170-5179.
- [2]. Golenbock DT, et al. Lipid X protects mice against fatal Escherichia coli infection. Infect Immun. 1988;56(4):779-784. [Content Brief]
- [3]. Golenbock DT, et al. Elimination and tissue distribution of the monosaccharide lipid A precursor, lipid X, in mice and sheep. Antimicrob Agents Chemother. 1988;32(1):37-41. [Content Brief]
- [4]. Golenbock DT, et al. Lipid X ameliorates pulmonary hypertension and protects sheep from death due to endotoxin. Infect Immun. 1987;55(10):2471-2476. [Content Brief]
