Lipid X

• CAT Number: I030845
• CAS Number: 86559-73-1
• Molecular Formula: C34H66NO12P
• Molecular Weight: 711.87
• Purity: 98%
• Synonyms: Lipid X
• Target: Bacterial
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: [(2R,3S,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5-[[(3R)-3-hydroxytetradecanoyl]amino]-6-phosphonooxyoxan-4-yl] (3R)-3-hydroxytetradecanoate
• InChI: InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1
• InChIKey: HEHQDWUWJVPREQ-XQJZMFRCSA-N
• SMILES: CCCCCCCCCCC[C@H](CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)O)CO)O)OC(=O)C[C@@H](CCCCCCCCCCC)O)O

Lipid X（Cat No.:I030845）is a synthetic molecule and a precursor of lipid A, a component of the bacterial outer membrane. It mimics the structure of lipid A and is used primarily in research to study the interaction between lipopolysaccharides (LPS) and the immune system. Lipid X has been investigated for its potential as an immune modulator, particularly in reducing inflammation. It has shown promise in inhibiting the activation of Toll-like receptor 4 (TLR4), which plays a key role in initiating immune responses to bacterial infections. Lipid X is explored for potential therapeutic applications in endotoxemia and sepsis.

Reference

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2: Golenbock DT, Ebert S, Will JA, Proctor RA. Elimination and tissue distribution of the monosaccharide lipid A precursor, lipid X, in mice and sheep. Antimicrob Agents Chemother. 1988 Jan;32(1):37-41. PubMed PMID: 3348611; PubMed Central PMCID: PMC172094.
3: Brozek KA, Bulawa CE, Raetz CR. Biosynthesis of lipid A precursors in Escherichia coli. A membrane-bound enzyme that transfers a palmitoyl residue from a glycerophospholipid to lipid X. J Biol Chem. 1987 Apr 15;262(11):5170-9. PubMed PMID: 3549717.
4: Golenbock DT, Will JA, Raetz CR, Proctor RA. Lipid X ameliorates pulmonary hypertension and protects sheep from death due to endotoxin. Infect Immun. 1987 Oct;55(10):2471-6. PubMed PMID: 3308707; PubMed Central PMCID: PMC260732.
5: Romano M, Hawiger J. Interaction of endotoxic lipid A and lipid X with purified human platelet protein kinase C. J Biol Chem. 1990 Jan 25;265(3):1765-70. PubMed PMID: 2295655.
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7: Pohlman TH, Winn RK, Callahan KS, Maier RV, Harlan JM. A glycolipid precursor of bacterial lipopolysaccharide (lipid X) lacks activity against endothelial cells in vitro and is not toxic in vivo. J Surg Res. 1988 Aug;45(2):228-37. PubMed PMID: 3043110.
8: Young HE, Zhao J, Barker JR, Guan Z, Valdivia RH, Zhou P. Discovery of the Elusive UDP-Diacylglucosamine Hydrolase in the Lipid A Biosynthetic Pathway in Chlamydia trachomatis. MBio. 2016 Mar 22;7(2):e00090. doi: 10.1128/mBio.00090-16. PubMed PMID: 27006461; PubMed Central PMCID: PMC4807358.
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10: Burhop KE, Proctor RA, Helgerson RB, Raetz CH, Starling JR, Will JA. Pulmonary pathophysiological changes in sheep caused by endotoxin precursor, lipid X. J Appl Physiol (1985). 1985 Dec;59(6):1726-32. PubMed PMID: 4077781.
11: Lipka G, Hauser H. Phase behaviour of mixtures of lipid X with phosphatidylcholine and phosphatidylethanolamine. Biochim Biophys Acta. 1989 Feb 27;979(2):239-50. Erratum in: Biochim Biophys Acta 1989 Mar 13;979(3):379. PubMed PMID: 2923879.
12: Smith RM. Pulmonary oxygen toxicity in rats: prevention by pyrogenic diphosphoryl lipid A and potentiation by nontoxic monophosphoryl lipid A and lipid X. Res Commun Chem Pathol Pharmacol. 1988 Nov;62(2):221-34. PubMed PMID: 3075066.
13: Lam C, Hildebrandt J, Schütze E, Rosenwirth B, Proctor RA, Liehl E, Stütz P. Immunostimulatory, but not antiendotoxin, activity of lipid X is due to small amounts of contaminating N,O-acylated disaccharide-1-phosphate: in vitro and in vivo reevaluation of the biological activity of synthetic lipid X. Infect Immun. 1991 Jul;59(7):2351-8. PubMed PMID: 1646770; PubMed Central PMCID: PMC258017.
14: Cho J, Lee CJ, Zhao J, Young HE, Zhou P. Structure of the essential Haemophilus influenzae UDP-diacylglucosamine pyrophosphohydrolase LpxH in lipid A biosynthesis. Nat Microbiol. 2016 Aug 15;1(11):16154. doi: 10.1038/nmicrobiol.2016.154. PubMed PMID: 27780190; PubMed Central PMCID: PMC5081216.
15: Golenbock DT, Leggett JE, Rasmussen P, Craig WA, Raetz CR, Proctor RA. Lipid X protects mice against fatal Escherichia coli infection. Infect Immun. 1988 Apr;56(4):779-84. PubMed PMID: 3278981; PubMed Central PMCID: PMC259370.
16: Aschauer H, Grob A, Hildebrandt J, Schuetze E, Stuetz P. Highly purified lipid X is devoid of immunostimulatory activity. Isolation and characterization of immunostimulating contaminants in a batch of synthetic lipid X. J Biol Chem. 1990 Jun 5;265(16):9159-64. PubMed PMID: 2345168.
17: Vyplel H, Scholz D, Macher I, Schindlmaier K, Schütze E. C-glycosidic analogues of lipid A and lipid X: synthesis and biological activities. J Med Chem. 1991 Sep;34(9):2759-67. PubMed PMID: 1895296.
18: Danner RL, Eichacker PQ, Doerfler ME, Hoffman WD, Reilly JM, Wilson J, MacVittie TJ, Stuetz P, Parrillo JE, Natanson C. Therapeutic trial of lipid X in a canine model of septic shock. J Infect Dis. 1993 Feb;167(2):378-84. PubMed PMID: 8421172.
19: Metzger LE 4th, Lee JK, Finer-Moore JS, Raetz CR, Stroud RM. LpxI structures reveal how a lipid A precursor is synthesized. Nat Struct Mol Biol. 2012 Nov;19(11):1132-8. doi: 10.1038/nsmb.2393. Epub 2012 Oct 7. PubMed PMID: 23042606; PubMed Central PMCID: PMC3562136.
20: Birkland TP, Cornwell RD, Golenbock DT, Proctor RA. Comparative study of lipopolysaccharide-, lipid IVa-, and lipid X-induced tumor necrosis factor production in murine macrophage-like cell lines. Adv Exp Med Biol. 1990;256:399-402. PubMed PMID: 2327296.