Lipid X | CAS#86559-73-1 | monosaccharide precursor

MedKoo Cat#: 598952 | Name: Lipid X

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lipid X is a monosaccharide precursor of E coli lipid A.

Chemical Structure

Lipid X

CAS#86559-73-1

Theoretical Analysis

MedKoo Cat#: 598952

Name: Lipid X

CAS#: 86559-73-1

Chemical Formula: C34H66NO12P

Exact Mass: 711.4323

Molecular Weight: 711.87

Elemental Analysis: C, 57.37; H, 9.35; N, 1.97; O, 26.97; P, 4.35

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Lipid X;

IUPAC/Chemical Name

(2R,3S,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5-(3-hydroxytetradecanamido)-6-(phosphonooxy)tetrahydro-2H-pyran-4-yl 3-hydroxytetradecanoate

InChi Key

HEHQDWUWJVPREQ-JIMHHRIFSA-N

InChi Code

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

SMILES Code

O[C@H]1[C@H](OC(CC(O)CCCCCCCCCCC)=O)[C@@H](NC(CC(O)CCCCCCCCCCC)=O)[C@@H](OP(O)(O)=O)O[C@@H]1CO

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 711.87 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Danner RL, Joiner KA, Parrillo JE. Inhibition of endotoxin-induced priming of human neutrophils by lipid X and 3-Aza-lipid X. J Clin Invest. 1987 Sep;80(3):605-12. PubMed PMID: 3624479; PubMed Central PMCID: PMC442281. 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. 6: Lam C, Schütze E, Walzl H, Basalka E. Protection of mice against lethal endotoxemia by lipid X is mediated through inhibition of neutrophil function. Circ Shock. 1987;22(4):311-21. PubMed PMID: 2820606. 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. 9: Lipka G, Demel RA, Hauser H. Phase behaviour of lipid X. Chem Phys Lipids. 1988 Oct;48(3-4):267-80. PubMed PMID: 3242955. 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.